Wholesome Crossdresser



""Ruka Urushibara. The mannerisms and voice of a woman...No. More feminine than any woman. But he's a guy. Taller than Mayuri, but so very thin...but he's a guy. Looks great in a shrine maiden outfit...but he's a guy! (Beat) ...He's a guy.""

- Steins;Gate

Crossdressing characters who are presented in a positive (or at least neutral) way. Frequently presented as Attractive Bent Gender (or at least not unattractive), relatively "normal" people as opposed to perverts or sexual deviants.

Some permutations of the trope are more or less unique to Japanese works. The Japanese Wholesome Crossdresser is usually well-groomed, compassionate, nice, and above all, so convincing that their "true" gender is only mentioned on occasion, as a reminder to newer members of the audience. There's a fair chance someone will get a crush on them, although this is usually resolved after The Reveal.

The opposite of Creepy Crossdresser. May overlap with Disguised in Drag or its Distaff Counterpart, Sweet Polly Oliver. (If the character wears crossdressing disguises more often than seems strictly necessary, this trope may apply.) Wholesome Crossdressers tend to enjoy dressing, even if only reluctantly, secretly, or subconsciously.

Generally does not overlap with Drag Queen (which is more about "performance" and theatricality) or Transsexual (usually a much deeper and more complicated condition), though there are exceptions.

Anime and Manga
"His Mom: Could this gorgeous woman be my son? O-Nui: So pretty! Sweet, I'm so gonna take him viral! Oise: What a beautiful woman.... Darling, I have to ask, do you ever see yourself on stage?"
 * Astro Boy examples:
 * Astro disguised himself as his sister Uran in "The Greatest Robot in the World" (Tetsuwan Atom, 1963), which likely makes him anime's first crossdresser.
 * In the original manga story and the 1980s anime, Uran disguised herself as Atom/Astro so she could fight Pluto in his place.
 * Kousaka from the Genshiken crossdresses to help the club sell doujinshi at a comic festival. His club mates find it disturbingly convincing.
 * Genshiken Nidaime introduces Hato Kenjirou, who crossdresses far more often.
 * The very girly Aoi Futaba from You're Under Arrest (who dresses as such after some self-discovery involving extensive undercover work) is virtually indistinguishable from the other female characters; post- Art Evolution his only barely male noticeable trait is being taller than other policewomen.
 * While Aoi's actual taste in partners doesn't come up much, one episode does have him seemingly worried a recent male E-friend will find out he's not actually a woman. Most fans simply assume this simply because of the common okama stereotypes.
 * Aoi is more of a Transsexual then a simple crossdresser though.
 * A running joke in Koko wa Greenwood (aka This Is Greenwood) is Shun being mistaken for a girl. His younger little brother is likewise androgynous enough to be distracting.
 * Hibiki-sensei in I! My! Me! Strawberry Eggs, who crossdresses in order to get a job from a man-hating boss. His Mentor is also a transvestite whose failed marriage to the boss caused her man-hating.
 * Chou Ryuuen aka Nuriko in Fushigi Yuugi. His actual gender is revealed pretty early on in the series.
 * Bishounen Hotohori, while usually just mistaken to be a woman (especially by Miaka during their first meeting), with minimal effort he has on occasion been a Wholesome Crossdresser . He had to enamor a band of thugs by pouring drinks for them (he only had to powder his face) and in the manga when he, Miaka and the Suzaku Seishi visited a females-only public bath where all of the males were temporarily WholesomeCrossdressers (he and Nuriko were the only men convincingly looking like women, to the chagrin of the others).
 * Like her Video Game counterpart  of Persona 4: The Animation is one of these.
 * Ouran High School Host Club subverts this fairly well. Haruhi is mistaken for a male by the host club at first due to her grubby and vaguely masculine clothing. However, Haruhi never bothers to correct them until they find out and doesn't have any problems with people mistaking her for a male. She simply has a wide concept of gender and doesn't mind dressing in a variety of costumes of both sexes.
 * Her father Ryouji (aka Ranka) is a slightly more traditional Wholesome Crossdresser, who works at an okama bar. At one point he violently shoots down Tamaki's idea that the club crossdress to get into Lobelia School, since 'amateur crossdressing' is an insult to the profession.
 * Mizuho in Otome wa Boku ni Koishiteru. He's so frightfully good at it, he makes all the girls gay for him. Or something. Even the animators seem to forget his gender occasionally, judging by the swimsuit scene.
 * Mizuho is wearing a fake chest, although it is very convincing.
 * Hell even in one of the later episodes where one of the other characters is looking through her old picture album, we see him (as a little kid) in a girl's swimsuit.
 * Alice in Mariasama ga Miteru.
 * Ciel from Black Butler. In episode 4 of the anime, he sneaks into a ball in a very...special outfit. Keep in mind that he's a a twelve-year-old boy]] who runs his own company. This outfit is infamous in the series, to the point of where it even has it's own fanbase and cosplay design. Heck, it's much more famous and recognized than even his regular clothes. It's really saying something when, by searching the term "Ciel Phantomhive" in Google Images, 99% of the pictures that pop up are of him in that outfit. Anyone who didn't know the series would probably be under the impression that he is a she. Alois is probably a better example, since he willingly wore his maid's uniform to get Ciel's attention and get him alone and away from his own party.
 * Jun from Happiness! (this article's cover girl boy) makes such a realistically pretty girl he even has several male students in his fanclub. Jun's only feature of maleness is the cast reminding us of it. The only obvious feature changed when he became a girl briefly is a larger chest, and he still had to mention it to his classmates.
 * In the original, adult-rated Visual Novel Re:Lucks sequel/fandisc to the original Visual Novel, he's effectively the Gay Option
 * Dori and Gura from Utawarerumono, though this is only revealed in the game.
 * Even then it is still confusing, as they are the ONLY males shown in the whole series to have tails. At the very least they seem to like men...
 * Tsubasa Kurenai from Ranma One Half, who's in love with Ukyo Kuonji, a Bifauxnen female crossdresser. A later character, Konatsu, also falls into Ukyo's orbit. It should be noted that Konatsu appears as a traditional Japanese kunoichi or female ninja.
 * Of course, Konatsu was raised to think of himself as a girl (even covering his bare chest and squealing) with very few concessions to his masculinity. Tsubasa, on the other hand, is a Master of Disguise who can be anything from a mailbox to a tree... but he prefers to wear a schoolgirl uniform underneath, rationalizing that if Ukyo chooses to dress like a man, then he should dress like a girl to match. Note that both characters were wholly mistaken for female until the very last page of their introduction stories, although they never actually claimed to be girls. Although, in Tsubasa's case, his appearance was so convincing that, unaware that Ukyo had met him while going to a boys only school to further her own "masquerade", they initially believed him to be a girl who had mistaken Bifauxnen Ukyo for a real boy. Then they thought that "she" was a lesbian after they learned he had known Ukyo was really a girl all along (which greatly startled Ukyo herself, who had evidently figured that Tsubasa was a crossdressing homosexual guy who had been fooled by her disguise).
 * Later in the manga, Ranma, Ryoga, and a couple other characters must distract the Yamata No Orochi, which has a taste for women. Therefore, they (as men, even Ranma) dress up as female stereotypes: a schoolgirl, a nurse, a meter maid, and a bride. Akane, meanwhile, crossdresses as a man to avoid being eaten.
 * Also a special note is to be made of Ranma him/herself. Although the Chinese uniform he tends to wear is generally thought of as genderless, he will often end up being turned back to male while wearing feminine attire (much to his chagrin and ridicule.) On the other hand, standalone character illustrations, cover art, and chapter breaks tend to depict female Ranma as unusually feminine.
 * However it depends whether or not it consider crossdressing since through magic, Ranma can be completely biologically female or male at anytime.
 * Either way he does seem to spend a lot more time being a woman than strictly necessary, and several gags are made out of him willingly dressing up in some very effeminate clothes and seemingly enjoying it.
 * Revolutionary Girl Utena's Utena Tenjou is a girl-dressed-as-a-boy example. Her choice of attire doesn't really do anything to hide her femininity, though, being more a matter of preference due to her desire of one day becoming a Prince Charming.
 * In the Mai-Otome manga, Princess Mashiro is replaced by her twin brother. The gags of the manga constantly poke fun at "Manshiro's" plight.
 * Randoh/Yuna from Pretty Face.
 * Justified/handwaved in that he was surgically rebuilt from a disfigured near-corpse to look like a teenaged girl.
 * Seki from Doki Doki School Hours likes to dress up in womens' attire - actually hoping he will impress girls that way.
 * From Kino's Journey is Even she does this herself sometimes.
 * Shugo Chara has, ironically but not unpredictably, Nadeshiko; her relatives explaining this is a technicality of her family's dance career. The only two hints at this is her transformation is into a polearm-wielding maniac, similar to Tadase's ironic change, and not swimming. Interestingly, she is Put on a Bus before anyone but the audience finds out (Amu is just smitten with her 'twin brother' for the day) though seems amused when she thinks how she'll officially explain it to Amu when she returns.
 * Interestingly, at this point there's more than a few gags that the show was becoming a Cast Full of Pretty Boys in regards to the 'normal characters', with the fairies teasing Amu's rampant habit of crushing on everyone.
 * Makoto/"Mako-chan" in Minami-ke. All it seems to take is a hair clip and a skirt and bam! Uncannily cute & convincing girl. Like, "make you doubt your own preference" convincing. Interestingly, his first comment in the second season is being glad he can dress normally again... and Gilligan Cut to him in a girl's outfit, with the comment the girls can't accept him otherwise.
 * You missed the part where Kana took one look at Normal!Makoto and shut the door in his face.
 * Yellow Belmont from Mospeada (Lancer/Yellow Dancer in Robotech).
 * In several episodes of Hayate the Combat Butler, poor Hayate is forced by Nagi to crossdress in blatantly female costumes like sailor fuku or a catgirl costume. The fact that Hayate's physical and facial features are sexually ambiguous mean that some of the male characters may get the wrong idea... Hayate's tendency to act Moe Moe in these types of situations doesn't help, either.
 * It's so wholesome that he actually has a male over the top in love with him. He ends up crushed when Hayate is exposed as a man...for all of half of chapter before turning "It's okay if it's you".
 * Fruits Basket features several wholesome crossdressers. Among the males of the Sohma family: Ritsu always wears women's clothing out of insecurity, Momiji dresses as a girl just because he likes it, and Ayame is an equal-opportunity sort who runs a fetish costume shop.
 * Subverted in the case of : shortly after we learn they are a Villainous Crossdresser, they turn into the wholesome (or at least emo) variety.
 * Azami in Himawari! is a male spy at an all-girls' ninja school, and wears the appropriate clothing. Everyone knows he's a guy and doesn't mind, because the whole spy thing means inside info for both sides.
 * Hamaji in H2O [[Footprints in the Sand]], who ends up marrying his best (female) friend, fathers a child, and *still* dresses like a girl. That's not something you see all the time.
 * There's quite a few of these in Family Compo -- the main character's adoptive family (his aunt and uncle) turn out to be gender-swapped -- that is, the extremely masculine uncle is biologically a woman, the extremely feminine aunt is biologically male. Their daughter switched genders every few months as she was growing up, until deciding to stay female when she entered college -- but the main character's not sure what she is biologically, which leads to most of the tension between them. The main character's also effeminate to the point that he ends up as the female lead in a student film, with a lesbian chasing him around, with a yakuza boss trying to convince him to get the "big snip"!
 * Both of the leads of Penguin Revolution are Wholesome Crossdressers. Ryo Katsuragi is obliged by his (rather quirky) talent agency to attend school as "Ryoko," and after she learns his secret and agrees to help him by acting as his personal agent, Yukari Fujimaru is obliged to dress as a man since the agency doesn't employ women as agents. Hilarity Ensues.
 * Racine Blanche Volban in Glass Fleet assumes her brother Michel's identity after his death in battle, and passes herself off as a man thereafter. In the process she also acquires her brother's Stalker with a Crush, who is a bit put out when he discovers that "Michel" is a woman.
 * Nagisa and Ryunosuke from Urusei Yatsura, a boy and girl who are forced to crossdress by their fathers and in an arranged marriage with each other, all so that Ryunosuke's family tea shop will stay in the family.
 * Yuki Nomura from the manga No Bra is a sweet, kind, beautiful and roommate Masato Kataoka's perfect girl. Except she's a he.
 * Ayase from Okane ga Nai is already mistaken for a girl when he dresses normally, in the manga he dresses up as a girl at one point thus becoming virtually impossible to be identified as male.In his case it might not be all that surprising that this earns him a severe stalker who is not bothered to learn his real gender and proceeds to stalk him anyway.
 * Gundam examples:
 * Laura Rola in Turn a Gundam.
 * In a possible homage to Laura Rolla, Gundam 00's dons a dress, long hair extensions, and a large set of fake breasts at one point in the second season. Why? So that
 * Alto Saotome from Macross Frontier used to be a Kabuki actor before he became a pilot. As a result, he retains a very feminine look even when wearing male clothing. This is Lampshaded by his friends, who often tease him and call him "Princess Alto" due to his appearance. People who don't know Alto will sometimes mistake him for a girl. It doesn't really help when some fans admit that they find Alto hotter and more attractive than his own mother.
 * Taken to a higher level in the second movie where Also.
 * In Fairy Tail, after the Council orders the arrest of Erza (after the incident involving Lullaby and the sheer amount of collateral damage it caused), Natsu decides to break into the trial dressed as her and admitting guilt, so as to get her off the hook. Needless to say, the real Erza is mortified.
 * Subverted in one chapter of Jo Jos Bizarre Adventure. The main character of Part 2, Joseph, cross-dresses as a tequila girl for a disguise to fool the Nazis. He fails to realize that most women aren't quite as well-built as he is. Hilarity Ensues.
 * In a slightly more feminine example, Narciso Annasui from Part 6 is a very effeminate-looking crossdresser, although the "Wholesome" part is highly up for debate here. While he is one of the good guys and seems to be genuinely in love (although his courtship methods are...strange, to say the least) with the main character, Jolyne, he is also an insane killer who has an obsession with taking objects and people (including his old girlfriend and the man she was caught cheating with) apart. He may even fall under Villainous Crossdresser, depending on who you ask.
 * Interestingly enough, he was originally intended by Araki to be female upon his introduction, only later being retconned to a male crossdresser. Over time, his appearance becomes much less feminine as well, with him pretty much being fully masculinized by the end of Stone Ocean (other than the women's clothes, of course).
 * Eiji Shigure in Gravion, while not a crossdresser by custom, ends up disguised (or at least dressed) like a woman quite a few times over the course of the series.
 * Yozak from Kyou Kara Maou!, though taller and more muscular than his fellow bishounen, loves to disguise himself as a woman. A cheerfully flirtatious woman, even.
 * Mahou Sensei Negima combines this with Instant Cosplay Surprise, with the girls dressing Negi up as a surprisingly cute fox girl. It sure gave Ayaka a massive nosebleed.
 * Negima?! Neo gives us Cheerleader Negi in chapter 19. [[media:Cheerleader_Negi_2668.jpg|As seen here, he's not the only one in drag (hint: the other one's wearing bandages around her chest).]]
 * Happens again in Chapter 17 of A Day Indoors..
 * In Clannad After Story, Misae's friends had a bit of fun sneaking Shima-kun into their school wearing a girl uniform, ending up with someone that made them jealous for being so pretty while watching him turn the heads of every male they passed.
 * Hans of "The Daughter of Twenty Faces" does this, albeit unwillingly, for a circus act the nakama are producing in episode 5 of the anime.
 * Tokyo Godfathers' Hana is a woman who insists that "God made a mistake" by putting her in the body of a man. In fact, a former professional drag queen, and probably the best groomed of the homeless bums who are our heroes - also the first to take the Trash Bin Baby to heart. Has an extremely Girly Run and a bass voice.
 * from Iria:Zeiram.
 * Husky from + Anima is introduced in the series as a pretty Mermaid Princess. Later you find out the pretty pretty princess is actually a boy cross-dressing for cash. Later, after being, he dresses up like a girl  Cooro and Nana come to , and neither of them can tell that the fish + anima is actually Husky in a wig and girly clothes until they get right up in his face.
 * One Piece examples:
 * The Kamabakka Kingdom is, quite literally, "full of transvestites". Even the animals are into it.
 * Mr. 2 Bon Clay. His fighting style is even called "Okama Kenpo"(Transvetite Fist Way), and he has no female partner in Baroque Works because "he counts as a man and a woman".
 * Izo, commander of the 16th division of the Whitebeard Pirates is probably the best example, as is maybe the only crossdresser who can't be spotted as one at first sight.
 * While they may be portrayed as nice people, they're also pictured to be rather unattractive. There are also quite a few jokes about them squicking out Sanji, so YMMV on the wholesome part.
 * Sanji was humiliated and tricked into becoming a crossdresser himself. Fortunately, he got better.
 * In the original Sailor Moon manga, Takeuchi admits to drawing Haruka (a protagonist and totally a woman) manly when posing as a man. At the same time, the original Starlights are just crossdressers and don't ever change gender. None of this stops either Haruka OR Seiya from forming crushes on Usagi, though.
 * W Juliet has Makoto Narita, the male lead, who dresses as a woman Also, his friend  Ito Miura might count, but she's more of a Bifauxnen (she never tries to keep her gender a secret, and she occasionally complains about almost always being cast as a guy in the drama club's plays).
 * Kiri in the manga Never Give Up inherited her father's facial features and build and has a tendency to act "princely" on occasion, but has a distinctly female personality and wears the girl uniform. Doesn't stop half the school's female population from developing huge crushes on her. However, in order to stay close to her love interest, the effeminate Tohya, she has to sign a modeling contract. As a male model.
 * Keiichi in Higurashi no Naku Koro ni is forced to crossdress on at least two occasions as part of the club's punishment games.
 * Coco from the Boku no Pico series crossdress on a daily basis. Pico and Chico do it more for the fun of it.
 * Noto Kanazawa aka Noto-sama, created by Axis Powers Hetalia's author Hidekaz Himaruya and the star of the short manga Advance! Kitakou Broadcasting Club. He's a cross-dressing School Newspaper Newshound who's often found stripping other people with his partner-in-crime, Yamato Nara from another Himaruya comic, Barjona Bombers.
 * It should be noticed that the Noto in the early Kitakou stories is virtually a completely different character. He isn't a WSC, just an Ordinary High School Student and a bit of a Butt Monkey, as well as being much less pushy. After the series added Pure to its title and Himaruya started drawing Barjona, Noto was revealed to be Cute and Psycho and snapped, starting on the path to his current incarnation. This era of the comic was taken off the website though, presumably due to Old Shame.
 * Koedo Chiba, a minor character in the Pure part of the series, is both this and a Bokukko. Due to having been made fun of as a child for looking like a boy, she opted to actually live her life as one.
 * As for Hetalia itself, Poland has dressed up in girls' clothes (usually miniskirts) in a few strips, which tends to weird out his Heterosexual Life Partner (or maybe not that heterosexual) Lithuania.
 * This is also part of Italy's backstory. Austria actually thought he was a girl until he hit puberty (it's somewhat implied that Hungary found out at some point, as she doesn't seem to be fazed by the discovery), and his first love Holy Roman Empire never found out that Italy was a male, always believing him to be a girl even when he left.
 * The child versions of Canada, Romano, and the US wore similar outfits. It's a Historical In-Joke.
 * As of Hetalia Bloodbath 2010, we've also had Hong Kong in a maid dress, and China in a qipao.
 * On the FtM side there was Hungary as a teenager, though she even managed to confuse herself with it, and so is maybe more an example of Raised as the Opposite Gender or possibly even a borderline Transsexual...or maybe an entirely different trope known as "Hungarian Gender Confusion" in the fandom.
 * While Nanami's gender in Sukisho is never explicitly discussed, his clothing are mostly ambigious regarding gender, and the non gender specific pronouns of Japanese are of no help either, everyone treats him like the Yamato Nadeshiko he always acts like. His winter coat, pink bunny slippers, and the outfit he wears in the kitchen at home, places him firmly into crossdresser land.
 * Seiji of Midori no Hibi is forced to crossdress in an attempt to catch a molester on a train. Naturally, some acquaintances from school see him, and decide that he's hot.
 * Kouta is often forced to wear various female outfits by a female gang in the manga.
 * Aikawa of Prunus Girl is very convincing, but helpfully reminds everyone at least once a chapter that he's a guy in between teasing Maki and hinting at Recursive Crossdressing.
 * Haku from Naruto is on the borderline between Wholesome Crossdresser and Villainous Crossdresser being that he's an Anti-Villain.
 * From the fillers, there's Princess Toki of the Land of Birds, who is also impersonating her dead brother Sagi.
 * Butterflies, Flowers: Domoto's coworker and very close friend until she realizes he's a he.
 * Used as a one-off gag in Game X Rush, where the middle-class Memori is portrayed as a "Cinderella" as oposed to Yuuki's imagined wealth. Also, Memori dresses as a nurse to "avoid suspicion" and stay in the hospital after hours... to make sure Yuuki doesn't escae, of course.
 * Nakahara Tatsuki from Boku no Tsukuru Sekai, a Magical Projectionist teacher and Ritsuki's father, as revealed by the latter by calling him "Dad" in Volume 1, p. 8. His reasoning for his appearance is that he "is a professional Projectionist! I walk the fine line between the genders so as to not give anyone any strange preconceptions" (Volume 1, p. 8).
 * In Basquash, Princess Flora Skybloom takes off to the city, to watch the protagonist's development close-up. To hide the fact that she's royalty, she disguises herself as a boy, hiding her hair beneath a baseball cap and taking on the name Alan Naismith. She does a pretty good job of disguising it, too, except that she was unable to restrain her love for the extremely girly Idol Band, Eclipse.
 * Reborn of Katekyo Hitman Reborn. Then again, he's a baby, so he can get away with it.
 * Miyashita Masashi from Onii-chan to Issho (official English title: Me & My Brothers). His official reason for this is due to his profession as a romance novelist, whose demographic for his novels is women. Masashi constantly crossdresses and Cosplays as a means of better understanding the female mind and applying this knowledge to write successful stories. The real motivation is possibly revealed in the last chapter of the manga, where.
 * Ash from Pokémon has to dress as "Ashley" to get his Gym battle with Erika. Brock is fooled, but Pikachu isn't (scent, maybe?). Ash would go on to invoke this trope a couple more times, once as a Meido.
 * Souta from Working was this when he was little (he's the only son in the family and was raised like a girl), and then needed to do it again in ep 9 and 13.
 * Baka to Test to Shoukanjuu's Hideyoshi is one, naturally. But since he has an identical twin sister, the cast and us can let it slide. The fact that Hideyoshi's a boy, that is.
 * Nononono is a ski-jumping manga by the author of Elfen Lied. The heroine Nonomiya is crossdressing and passing for her dead twin brother because only men are allowed in professional ski-jumping... and she wants to win Olympic gold. Played very seriously.
 * Kotobuki Seishiro (Seiko!) from Lovely Complex is very nice and friendly (a little TOO friendly with Ootani) who insists "god made a mistake" and put her into a boy's body. After The Reveal and fending off a few hateful comments, Ootani, Risa, and friends take him/her in as part of their group. Aside from some friendly teasing (often by way of Haruka), Seiko seems to fit in and find a happy school life with little difficulty.
 * In The World God Only Knows  She even admits guys' clothes are better.
 * And she gave Keima female uniform, while saying that it is something he needs for their future. Keep in mind that she is trying to conquer him.
 * Fay in Tsubasa Reservoir Chronicle sometimes does this. In the Alternate Universe Omake first Drama CD, he is shown wanting to join the girls as they dressed in maid outfits for the school festival, and in a strip comic for New Year's he wore a female kimono borrowed from Yuuko. He comments that he did it in secret because Kurogane hadn't let him wear the maid costume. Also, in the main storyline, he wears what looks suspiciously like a wedding kimono during his stay in Nihon.
 * Levin from Tekkaman Blade.
 * Ayumu from Kore wa Zombie Desu ka?, as he's drafted into a Magical Girl army after his zombie nature absorbs most of Haruna's powers, including the ability to transform into a Masou Shoujo.
 * Sister from Arakawa Under the Bridge. The guy always uses a nun's habit and on one occasion he used a schoolgirl uniform.
 * A number of transvestites appeared in "Jupiter Jazz", an episode of Cowboy Bebop. One of them even returned for The Movie.
 * In the Fullmetal Alchemist manga, there's an automail engineer named Mr. Garfiel. Though initially he doesn't wear female clothes, only makeup, he puts on some lacy, poofy shirts later on. He also acts overly feminine, even compared with the manga's normal female cast. He also frequently flirts with Ed and other male characters.
 * Wandering Son has this as a large part of its plot, as a feminine boy, Shuichi, and a tomboyish girl, Yoshino, begin frequently dressing in girl's and boy's clothing respectively, much preferring and wishing to be the other gender. They also befriend a Transsexual named Yuki, who acts as a Cool Big Sis to them.
 * More accurate examples, gender-wise, would be Chizuru and Makoto. Makoto makes a cute girl when he dresses up, even though he thinks he looks bad due to his freckles and glasses (which isn't a bad thing). Chizuru is a girl who sometimes crossdresses as a boy, and she looks like androgynous.
 * Oscar from Rose of Versailles is another example of the girl-raised-as-a-boy plot device.
 * Makoto Mizuhara from El-Hazard: The Magnificent World, Yakumo from 3x3 Eyes and Yellow Belmont aka Lancer from Genesis Clumber Mospeada/Robotech Third Generation crossdress as a plot necessity rather than for their personal tastes. I.e.: Lancer crossdresses and poses as a female Idol Singer to act as a spy for the resistance group he's a part of.
 * All of the "princesses" in Princess Princess.
 * The tenants, particularly Yuki, frequently dress up as women for various convoluted reasons in The Wallflower.
 * The Slayers does this once a season, one episode per season (except seasons 4-5). Fans of the series refer to this as Episode 17, as each crossdressing episode is the seventeenth episode in the given season. Ironically, not just the male cast, but often support characters introduced in the episode itself as well. Perhaps the most bizarre example is the "drag-on" sea dragon in the first season, who Gourry defeats by scratching its face and forcing the dandy dragon to retreat lest it gain any defacing scars.
 * Kazuki in GetBackers. The writers, especially in the anime, will take any excuse they can to get him into womens' clothing. Sometimes it's a misunderstanding, sometimes it's part of his job, sometimes it's favor for a friend... and then there's the official art of him in womens' swimsuits. The anime went so far as to lampshade it in the fourth ending: there are two points where the characters are divided by gender, and he's with the girls both times. To be fair, he's mistaken for a woman when he's not explicitly crossdressing.
 * Gintama has the Okama bar that created the lovely Paako and Zurako. Gintoki, Shinpachi and even Kagura have no problems crossdressing when they need to...or just for the hell of it, actually. And there's also.
 * Eyeshield 21 had Ootawara and Sakuraba dressed as maids (during a public practice) as a punishment for losing a trivia game during a school festival. This, however, only increased Sakuraba's popularity. Hiruma also dressed like a maid to spy on the players from the American team. Panther got a good laugh out of it.
 * In the Black Cat anime, both Train and Sven are shown crossdressing. For Sven, he wears a very frilly, fancy dress to try to lure a killer for a bounty. It doesn't work. For Train, after transforming into a child, while Eve and Kyoko go out to buy clothes the right size for him, he's forced to wear Eve's dress.
 * Neon Genesis Evangelion's main character Shinji Ikari has crossdressed on two occasions, once wearing Asuka's spare plugsuit (complete with breast plates) and again when he and Asuka are training to defeat Israfel they wear identical ... "jazzercise" outfits.
 * In Shinji Ikari Raising Project, Asuka and Rei find him even more attractive when he is forced to wear a dress. Do they get a bonus point for Les Yay?
 * Yozak from Kyo Kara Maoh is a 'spy' who crossdresses on a regular basis, to the point where he now carries a dress around just to have one handy. Which is quite hilarious, seeing as he's ripped and rather manly.
 * Ryo Hayama of Bremen fully dresses up as a girl which includes wigs, fake boobs, platform shoes, fake nails, etc. Just beware about calling him one.
 * Cruz, from NEEDLESS, unwillingly cross dresses as a girl in the later part of the manga (and ended up popular with his team mates as well as the readers) in order to infiltrate an all-girls Academy. Later he gets a bounty on his head and had to remain cross dressing as a girl to avoid attention from his enemies. Its not known whether he will ever revert back to male clothing as his team mates protest against it when he mentions about it, thus he is STILL in girl's clothing. A popular nickname for this version of him is "Yamada-ko"
 * In There Beyond the Beyond, Futaba admits that wearing girly clothes doesn't bother him, because his older sister makes him do it all the time.
 * From +C: Sword and Cornett, there's multiple instances of this; both Belca and Eco have had to cross-dress to escape the public eye, and while for the most part it's a disguise, it appears that yes, they're very much this trope. In his youth, Eco apparently went out to drag contests, and  Belca, dressed a girl (though he's wholely unwilling), accidentally has someone fall in love with him, and Musca's likewise called him a pretty lady. Eco says himself that Belca makes for a pretty girl -- not a pretty as himself, of course.
 * En Shinohara from Usotsuki Lily has such a strong dislike for men that he can't even look at his own reflection. It's for this same reason that he takes up crossdressing. Hilarity Ensues as the series is about he and his new girlfriend trying to work around the issues this causes.
 * An enemy example occurs in one episode of Yu Yu Hakusho. Yusuke and company are storming the compound of a demon-exploiting tycoon and have to have off with his guards. One of them appears to be a girl named Miyuki (and honestly looks like such), so Kuwabara backs down while Yusuke holds no such qualms. During the fight, though, a quick grope up top and down below told Yusuke he didn't need to take it easy on him, so he didn't. The only dirty looks later were directed towards Yusuke for acting like a pervert.
 * Kaichou wa Maid-sama: Aoi Hyoudou.
 * Yukimura as well, although in his case it's a matter of periodically being forced to crossdress (very convincingly) by the other characters rather than doing it of his own initiative. You can have three guesses as to what kind of aura other characters feel from him (despite his best efforts) and the first two don't count.
 * G in From Eroica with Love.
 * Shizu in Maria Holic. Of course, she only crossdresses when attending classes (she and her brother are in a competition with each other, and part of the competition involves attending both a boys' school and a girls' school during their high school years).
 * Not one to be outdone by her middle class scholarship namesake, Haruhi Suzumiya has her moment when she's allegedly Disguised in Drag in chapter 3 of Disappearance (guess whose gym tracksuit she wears as her disguise?).
 * In Oh! Edo Rocket the reason for Genzo's crossdressing is never explained, but it might be an attempt to get people to notice him. Though his hair and makeup are very feminine from the beginning, he doesn't actually dress in women's clothes until near the end of the series after his mother has sold all his clothes and the only thing left for him to wear is a dress. The reactions to this are overwhelmingly positive, and he then goes on to play the female lead, Princess Moonbeam, in a play that sums up the events of the series.


 * Nezumi from No. 6 frequently has to dress as a woman in order to perform his act in plays, and makes a rather convincing woman at that.
 * The main cast of Otoko No Ko Wa Meido Fuku Ga Osuki are four brothers who help their parents' Maid Cafe, and dress accordingly. The middle brothers usually crossdress only for work or other cafe-related business, while the oldest and youngest brothers crossdress all the time.
 * The titular character from Kunisaki Izumo no Jijou, who is already attractive enough to be mistaken as a girl all the time, frequently crossdresses as a result of him invariably receiving female roles from his family's kabuki troupe, much to his chagrin. His senior in the troupe, Kagato, is another one, although unlike Izumo he actually enjoys it.
 * Kou From Samurai High School.
 * Fire Emblem from Tiger and Bunny loves his pink angora, high heels, and makeup. He's also a successful Hero with fire-based superpowers, is the CEO of a major corporation, and acts as Team Mom for the rest of the cast.
 * Anna Graham of Phi Brain: Kami no Puzzle is an extremely girly boy, to the point that Daimon Kaito's childhood friend Nonoha starts to worry whenever Anna and Kaito are alone together, even after discovering his real gender. As for the "wholesome" part, Anna is a very friendly, sensitive artist, as well as a Friend to All Living Things turned Up to Eleven.
 * The two-part hentai manga series Secret Plot gives us a minor character named Yuya, who invoked this trope after his identical twin sister died in a car accident. His parents (who favored his sister over him) fell into alcoholic depression after her death, but then one day when Yuya came out of the shower, his mother saw him and mistook him for his sister (it helped that he had long hair). After this, he came home from school the next day and all of his own stuff was thrown out and his sister's stuff set up in its place. However, realizing that the mistake caused his parents to come out of their depression, he decided to just run with it, developing the habit of leaving home to go to school while dressed as a girl, then changing his clothes to appear as a boy outside the home, and changing back again before going home. By the time he finally confesses all this to his Love Interest, he's developed serious issues about the whole thing.
 * Minoru in AKB 49 Renai Kinshi Jourei crossdresses to join an all-girl idol group to watch over his crush who is in the same group and protect her dream, without her knowledge.
 * Makoto in Nicoichi crossdresses to act the mother role for his son, who due to his young age could not understand the fact that his mother has already passed on.
 * Itsuki of Heartcatch Pretty Cure spends half of the series dressed up as a guy and is usually seen in her male school uniform, mostly because she's determined to take over her grandfather's dojo while her older brother is sick. However, once her brother is cured and she takes up the role of the third Precure, she starts sliding back into more feminine roles, becoming a member of Erika and Tsubomi's fashion club and is seen in the Distant Finale wearing the school's female school uniform.
 * Lotte no Omocha has Naoya, who is reluctant about it, but give him a long haired wig and he has to fight off the guys.

Comic Books

 * Quality Comics's Madame Fatal, the first cross-dressing superhero. "She" was really Richard Stanton, retired actor, who took up the up the persona of a harmless-seeming old lady after his daughter was kidnapped. Because no-one suspects the old lady.
 * And then there's the Goddamn Maidman!
 * Superman's Pal Jimmy Olsen has disguised himself as a woman... more than a few times, actually. He's rather good at it.
 * George (who is either a crossdressing woman or a transgender man, the comic never elaborates) in Grant Morrison's Sebastian O is one of the more sympathetic characters in the comic. Not that the bar is particularly high.
 * Lord Fanny in Grant Morrison's The Invisibles, who was raised as a girl by her grandmother, a witch, because men could not become witches.

Fan Fic

 * Both Mitsuuru Takahashi and Shugo Kino in Pretty Cure Heavy Metal are this, with the only exception being when they're attending Isuten Junior High. Outside of school, Shugo takes the Real Women Never Wear Dresses trope to whole new levels, such as her swimsuit including short shorts and her Cure Hendrix costume including hot pants. Mitsuuru himself was forced to crossdress by his own parents, seeing that they were spending so much money on their firstborn Yuki alone, making it impractical, if not impossible, to buy new clothes for a second child, even if said second child was a boy. Despite being enrolled in MacArthur Grade School for the Arts as a boy, he had to wear his sister's old uniform. This continued for so long that by the time he was able to wear a boy's uniform for once when he attended Isuten Junior High, he was pretty much used to crossdressing and by that point was willing.
 * It's revealed in Pretty Cure All Stars 3D: Live and Loaded! How About That! that he looked so convincing as a girl (despite everyone knowing he's a boy) that he got a girl's role in every play his class held, including Sakura Kinomoto from Cardcaptor Sakura (referred to as "Cardcaptors" in the fic), a play mentioned in episode 29 of PCHM. This streak continued into his junior high years, and his most memorable performance was as Suzumiya Haruhi (in that play, Shugo portrayed Kyon).
 * Harveste Addams of the Harveste Series by kyaru-chan. Harveste, who has a conveniently gender nonspecific name, wears women's clothing mostly because she can hide more weapons in dresses than suits.
 * At one point in the third chapter of The Melancholy of Haruki Suzumiya, Haruki has Mitsuru wear a maid outfit for a photo shoot.
 * In the Hooker Verse, The Nostalgia Critic wears a corset and skirt. Of course, the 'wholesome' part is a little debatable given that he's, well, a hooker, but...
 * In one Neon Genesis Evangelion fanfic, Shinji raids Asuka's clothes to try out crossdressing in an effort to gain acceptance from his father who raised a girl instead of him. Of course, Asuka throws a fit when she finds out as she thinks Shinji and Kaworu (who happened to be on-scene) are doing perverted things (they aren't, the fic is entirely SFW); once she calms down, she offers to correct Shinji's appearance.

Film
""I'm supposed to be the Grand Duchess Anastasia, but I think I look more like the Chrysler Building.""
 * All three protagonists of The Adventures of Priscilla, Queen of the Desert, to varying degrees. Terrence Stamp plays a hard-drinking but patient transsexual, Guy Pearce a bitchy, high-strung Performance Artist, and Hugo Weaving is the timid, sweet-natured drag queen who persuades them to do a cabaret act in the middle of the desert. That breaking sound you heard was your brain.
 * To Wong Fu, Thanks For Everything, Julie Newmar has John Leguizamo, Patrick Swayze, and Wesley Snipes all as crossdressing drag queens. Vida and Noxeema even convince Chi-Chi to give up the boy she has a crush on to the girl in town that likes him, as it wouldn't be fair to him.
 * The Fifties comedy film Some Like It Hot. Originally Joe and Jerry did it to escape the Mafia, but they kept up the act... and Jerry took his new role very seriously.
 * In Takashi Kitano's Zatôichi, Geisha Seitaro 'Osei' Naruto is actualy a man.
 * Tootsie role, anybody? While Dustin Hoffman starts out playing a female simply in order to get work, he ends up playing the part in real-life as well.
 * In Trainspotting, Begbie makes out with a "woman" in his car for a while before discovering it's a man.
 * Kitten from Breakfast On Pluto (played by Cillian Murphy) basically personifies "cute".
 * Roger DeBris from The Producers.


 * Played more than usually straight in Ed Wood: Ed is shown to be a heterosexual who happens to find women's clothing more attractive and comfortable. This is probably because he was based on an actual person.
 * This was also how Ed Wood portrayed a thinly-disguised version of himself in Glen or Glenda.
 * One of the "edgy" things about Baz Luhrmann's modern remake of Romeo and Juliet is having Mercutio (plaued by Harold Perrineau) show up to the Capulets' ball - imagined in the remake as a Halloween party -- dressed in drag. He stays in drag for a lot longer than is really necessary. Then again, it's Mercutio.
 * And he also dances and lip-syncs to "Young Hearts Run Free". It's awesome.
 * Vilma in Taking Woodstock.
 * In Pret-a-Porter (Ready to Wear), Danny Aiello plays Major Hamilton, a buyer of sensible clothing for the Montgomery Ward catalog who is secretly a high-fashion loving transvestite. As he spends his days during Paris' fashion weeks buying up product for his company to sell to middle America his wife Louise, played by Teri Garr, combs the boutiques of the Champs-Elysees, searching for lovely things in XL for him. Near the end of the film they spend a quiet dinner together, both in couture gowns and make up and she tenderly compliments him for looking, "beautiful, like Barbra Streisand".
 * In both the film and the play of Victor Victoria, the lead is a woman who crossdresses as a male, then gets a job as a female impersonator in a burlesque show. Also an example of Recursive Crossdressing.
 * Saga in Mitt liv som hund (My Life as a Dog).
 * In Don Juan Demarco, the title character (played by Johnny Depp) is at one point enslaved, and sold to a lusty Sultana. To prevent the Sultan from discovering her new personal attendant is an entirely 'unaltered' male, she disguises her new toy (most fetchingly!) in a loose-fitting jeweled sari. (One could suspect that the script-writers invented this to showcase Depp's talent for female impersonation, but it's actually lifted from Lord Byron's epic poem Don Juan.)
 * In Waiting for Guffman, director Corky St. Clair might be a closeted example. He often buys clothes for his wife Bonnie, a reclusive lady who nobody ever seems to have met.
 * The title character of Rango wears a dress in order to pass as a travelling actor to get some arrest-ees to let their guard down. It turns into an elaborate wagon chase scene, with him still in the dress.
 * Disney's Swiss Family Robinson had Roberta, who was disguised as a cabin boy by her father to protect her from the pirates.

Literature

 * George, from the otherwise hilariously backward children's series The Famous Five by Enid Blyton.
 * The lovely Ms. Fate lives in the Nightside, and is a genuine old-school heroine who happens to be played by a man.
 * Salome "Sam" Fredericks in Tad Williams' Otherland series pretends to be a boy online, complete with Tomboyish Nickname, to avoid getting singled out for her gender. This causes complications when her friend, Orlando Gardiner, seeks her out in Real Life.
 * The briefly-appearing "Lillie Longtree" in Welkin Weasels: Vampire Voles is an actor who usually plays female roles, and wears a red riding hood when out walking in the forest "to confuse the beasties". It should probably be noted that Maudlin asks about this "with a touch of envy in his voice".
 * from The Lord of the Rings
 * Older Than Print: The medieval Arab and Turkish epics were replete with crossdressing -- both males as females and females as males. The legendary hero al-Battal crossdresses to sneak into the Greek emperor's palace, and his son Madhbahun disguises himself as a princess to lure the wily villain Uqba into his clutches. In Sirat Dhat al-Himma, the Muslim warrior queen dresses up as a priest and kisses the Greek princess Nura.
 * In The Walker Papers series by C.E. Murphy, Joanne's friend Billy Holiday is a crossdresser who is also a respected police detective and happily married with children.
 * Terence, the squire in Gerald Morris's The Squire's Tales, crossdresses to help rescue Sir Gawain from a dungeon.
 * Louis from The Extra Man.
 * Alanna from the Tortall Universe. During her time, girls were not allowed to be knights so she had disguise as one to receive training.
 * To an extent, Sally Sweet in the Stephanie Plum series. He's described as not exactly attractive and nearly every other sentence out of his mouth is a Cluster F-Bomb, but he is depicted as a basically nice guy (even if he's the only school bus driver around who carries an Uzi under his seat).
 * In the Evil Genius Trilogy Cadel crossdresses several times as a disguise, starting in his disguise class at the Axis institute and continuing whenever he needs to escape some kind of surveillance. He has a whole alternate identity for his female persona - Ariel Schaarp.
 * Yuki Ajiadou from CLAMP's light novel series CLAMP School Paranormal Investigators is a boy who dreams of becoming a famous actress. To that end,.

Live-Action TV

 * Boy Meets World examples:
 * In S4E15 ("Chick Like Me"), Cory plans on dressing as a girl to school in order to find out how life is different for female students and male students. He turns out to have too masculine of a walk, so Shawn tries teaching him how to act female, getting it "surprisingly on the nose" according to Topanga. When he shows Cory how to walk like a woman and gets it perfectly, Cory and Topanga decide that Shawn should be the one to dress like a woman for the day. He turns out to be a babe. He also has a preferred "female" name (Veronica) and admits to having thought about doing this a lot before Cory ever decided to write the article.
 * In the much later episode "What a Drag", Eric Matthews decides that the only way for him and his best friend to avoid a local psycho and his gang, after almost getting them arrested, is to crossdress. They immediately turn to Shawn for help, and Shawn gives them a whole series of tips on how to crossdress correctly, so he clearly hasn't stopped since. Eric also decides to continue crossdressing after the episode ends, just for his own sake. Notably, both characters are not only heterosexuals, they are actually three of the show's most prolific flirters.
 * Max Klinger on Mash was a wholesome, if definitely not attractive or believably female, crossdresser. He crossdressed in order to get a Section-8 "insanity" discharge from the Army. When Radar left, Klinger became clerk and dropped his cross-dressing gig. However, having worn women's clothing for so long he found that his body had gotten used to the feel and he developed a rash unless he wore female underwear under his uniform. There was a kind of 'don't ask-don't' tell policy about it.
 * On Hill Street Blues, Jeffry Tambor played a cross-dressing lawyer who was doing so on advice from his psychiatrist to "resolve his feminine-identity issues." (The "cure" worked, and the same lawyer later became a highly-respected judge on the series).
 * DEA Agent "Denise" Bryson on Twin Peaks, played by David Duchovny. (Who, as it turns out, has really nice legs.) Also a rare case of a heterosexual crossdresser on network TV.
 * Reality TV example: Derrick Barry of America's Got Talent
 * Clarence from Boston Legal crossdressed as both an alter ego, Clarice, and Oprah.
 * Drew Carey's brother on The Drew Carey Show, before marrying Mimi.
 * Subverted in Leave It to Beaver, where Wally is cast to play a saloon-girl in a "Summer Stock" Western; he hates the idea so much, that he ends up conning the perfect person for the role into taking it-- Eddie Haskell.
 * Also subverted in Comedy Central's series Strip Mall, a male character is seduced by a supposed cross-dresser (but who is actually played by a very obviously female woman).
 * Mr. Humphries of Are You Being Served. In one episode, he helped out by cross-dressing by pretending to be a female customer to help Mrs. Slocombe get her job back.
 * Charlie Watkins, a CONTROL agent on Get Smart, is such an exceptional undercover agent that he looks exactly like the Real Life (and 100% female) actress Angelique Pettyjohn, and is known as Agent 38 on account of his impressive bust measurements. Charlie's all man, though, and evidently quite heterosexual, as demonstrated by his flirting with Agent 99.
 * Once in Myth Busters, Tory wore a bra For Science!. Another time, while re-enacting a scene from Speed, he wore a wig. "Once again, making my parents proud."
 * In a BBC modern-dress production of The Taming of the Shrew, Petruchio was a rare Western media example of a heterosexual crossdresser.
 * This is a common occurence in Super Sentai series:
 * In an episode of Dai Sentai Goggle Five that featured dolls coming to life, Miki/Goggle Pink disguises herself first as a male clown with a painted mask and just a slight change in voice, and later successfully pulls off a handsome prince disguise via a wig and a fitting outfit.
 * Then, in Choujin Sentai Jetman, the one cross-dressing was... Raita/Yellow Owl, in order to trick a Monster of the Week who absorbs women's voices. He successfully pulls it off, too - apparently, even fatties can make convincing women with just some makeup, a wig, and a kimono.
 * Soutarou Ushirogame/GaoBlack in Hyakujuu Sentai Gaoranger also pulled off cross-dressing as a bride. Even if he ended up striking the sumo pose and "Dosukoi!" yell.
 * Tetsu/DekaBreak in Tokusou Sentai Dekaranger seems inordinately fond of dressing up as a woman during undercover missions. Both times he's done it, he's caught the eye of a creepy buglike minor criminal stalker...who didn't care that it was a trap when Tetsu revealed his true gender.
 * In Magiranger vs. Dekaranger, he and Hikaru have to cross-dress again, much to the shock of Urara. Jasmine however, is not surprised.
 * A more realistic approach is later revisited in Samurai Sentai Shinkenger, with Ryuunosuke/Shinken Blue. After all, he's a kabuki actor, thus cross-dressing is par on the course. It's even used in a Xanatos Gambit, and it helps that the actor (Hiroki Aiba) is a Bishonen by default. Ryuunosuke even said "he still has much to learn" after THAT much of a convincing act.
 * Then, the V-Cinema DVD Special took this to ridiculously funny levels, when in a bizarre (long story) moment, Kotoha and Mako dress and act like school boys... and then Ryuunosuke, Chiaki and Genta reveal that they're cross-dressers as well. The biggest WTF moment was when Takeru, who's calmly sitting... suddenly flips his clothes and reveal himself to be a rather CONVINCING cross dresser too. What. The. Hell.
 * Simone, the likeable twelve-year-old heroine of the Swedish children's programme Dårfinkar & Dönickar, based on the book by Ulf Stark, spends a while masquerading as a boy at school.
 * Jack Donaghy of 30 Rock reveals that he exclusively wore hand me downs until he was 12. His older siblings were all girls.
 * British soap Holly Oaks features Kris, a bisexual cross-dressing man.
 * Dave in Degrassi wore a long frilly skirt to prove a point when Adam made him uncomfortable.
 * Coronation Street, of all things, introduced Marc (aka, sometimes, "Marcia") in 2011, the show's first crossdressing character (though Hayley, introduced in 1998, is a recurring Transsexual character.) The show portrays Marc's dressing as both healthy and acceptable, with only unlikeable characters being against it.
 * The original premise of 80s sitcom Bosom Buddies was Disguised in Drag, but the boys carry on with the charade over the course of the series longer than seems strictly necessary.

Music
""''You really can't ignore her, And if you don't adore her, There might be something wrong with you!''""
 * The protagonist of the song "Cherry Lips" by Garbage.
 * "Lola" by The Kinks.
 * Desmond, the family man who "stays at home and does his pretty face" in "Ob-La-Di, Ob-La-Da" by The Beatles. Funnily enough, that lyric was a mistake made by Paul, but they left it in because they were sick of working on that song.
 * Pretty much everyone in Queen, in the video for "I Want to Break Free". Nice legs, Roger Taylor.
 * "Bitty Boppy Betty" by Pink Martini is about a charismatic district attorney who dresses as a woman on the weekends, and who is the toast of her local nightclub:

""''Who put the drag in drag queen? Don't knock it until you've tried it''""
 * Green Day's "King for a Day" (Princess by dawn!).


 * Kagamine Len is this in "Imitation Black" and other Visual Kei styled songs by natsuP. He arguably is in "Servant of Evil,"
 * Kaito in "The Madness of the Duke of Venomania" does this
 * The UTAU Ritsu Namine.
 * Brian Molko, the singer for the band Placebo. Easily passes as a woman. The protagonist of their song "Nancy Boy" also qualifies.
 * Mana from Malice Mizer is very convincing as a female, and reportedly does this full time.

Mythology

 * Lan Caihe of the Eight Immortals may or may not be one. It depends on who you ask.
 * According to some versions of the Minotaur's story, Theseus decides to switch two of the seven female victims with two very effeminate but brave boys disguised as girls. Said boys would have later fred the prisoners while Theseus was dealing with the Minotaur.

Tabletop Games

 * Exalted has a few cultural examples as part of the background:
 * In the West are the Tya, a "third gender" of women who adopt male social roles in order to work as sailors. This is mainly because the waters of the West are overseen by hag-like spirits known as storm mothers, who will try to sink any boat that's crewed by any woman prettier than themselves. Which is pretty much every mortal woman in Creation, and most of the dead ones.
 * The city of Chiaroscuro is overseen by the Delzahn, who are pretty firm on gender roles - men defend and supply the household, women run it but don't do much on the outside. However, it allows men and women the option of becoming Dereth - they basically can dress and act like the other gender, as long as they wear a gray sash at all times in order to avoid confusion.

Theater

 * William Shakespeare's comedies employ this trope rather often, partly owing to the nature of Elizabethan theatre in general. Women weren't allowed on stage by law, so female roles were played by male actors. Thus, when a female character is a Wholesome Crossdresser, as in Twelfth Night, she would have been played by a man playing a woman dressed as a man. The trope is taken even further in As You Like It, where Rosalind would have been a man playing a girl disguised as a boy pretending to be a girl.
 * Middleton and Dekker's 1610 comedy The Roaring Girl features one of these as a protagonist; unlike the cross-dressing heroines of Shakespeare's plays, though, she isn't disguised, and everyone in the play knows her real sex -- she just likes dressing like a man. (The real person she is based on was slightly less wholesome.)
 * Angel Dumott Schunard from Rent, who may also be Transsexual.
 * Fancourt forced to chaperone as the titular Charlie's Aunt.

Video Games

 * Bridget from Guilty Gear. The original story was that Bridget is part of a set of identical twins, which in his village were considered bad luck, and was sent to be a nun (either that, or he'd be abandoned to his death as a newborn), therefore his whole story path is him going Determinator and wanting to prove he wasn't a bad omen on anybody. His creator admits that making him a boy was, in the spirit of other characters in the game, to simply make him more interesting.
 * A common Image Macro used for Trolling shows a picture of him and says "Everyone's gay for Bridget". Very confusing if you haven't played the game. There's a reason Unsettling Gender Reveal used to be called "Dropped A Bridget On Him".
 * Despite his mannerisms and the promo art featuring him in feminine poses, Bridget does not actually identify as female. As far as he's concerned, he's just a boy in a habit who carries around a teddy bear and a yo-yo and really wishes people would stop thinking he's a girl.
 * qualifies as this from The Legend of Zelda: Ocarina of Time. Link has no idea he is not a man until The Reveal. Qualifies as a case of Sweet Polly Oliver.
 * The character of Vivian in Paper Mario: The Thousand-Year Door was, in the Japanese version, a male who appears female. In fact, the likeness was so good it took only a few text edits to scrub out the potentially offending element. Ironically, not many characters in the game even have features; Vivian himself is a faceless spectre with a big hat, lipstick, and curly hair.
 * And the original manual for Super Mario Bros 2 (the U.S. one) gives this Birdo description: "He thinks he is a girl and he spits eggs from his mouth. He'd rather be called 'Birdetta.'" Much like Vivian, in later games in the U.S. she's retconned into a girl, but in Japan s/he's a guy. Much more recently however, Nintendo of America has inched a bit closer to recognizing this issue.
 * Although not actually crossdressing, Lucius (a very androgynous man in unisex clothing) from the 7th Fire Emblem otherwise fits this trope, including people getting squicked out at him when the learn his true gender.
 * Persona 4
 * Another example would be
 * And on the topic of Persona, Persona2 has Jun Kurosu, who not only has cross dressing listed as one of his official profile talents, but also has a demon contact with Lisa dedicated to just how damn well he can cross dress.
 * The Magypsies in Mother 3, and, to a lesser extent, the girl they raised, Kumatora. Noticeably, the only Magypsy who doesn't crossdress is a traitor.
 * Faris from Final Fantasy V. One character even mocks her by saying, "We will fight like men! And women! And women who dress like men!" It doesn't help that she's probably the most masculine-acting of all of the player characters. The main character even mistakes her for a man.
 * It's not so much mocking as it is a playful jab. There's even a scene before you find out that the dude's a chick when  And yet they continue to be surprised when the big reveal comes.
 * It was probably a Stupid Sexy Flanders moment,
 * In Final Fantasy VII, hero Cloud Strife has to rely on the help of some friendly transvestites so that he can disguise himself as a woman and infiltrate a gangster's mansion.
 * From Suikoden V,
 * In Pokémon Crystal, if you choose the female trainer, the overworld sprite changes from female to male if you do any game link cabling with any of the other six games. Yes, even with another Crystal version.
 * Also, everyone in Gym Leader Janine's gym in (Heart)Gold and (Soul)Silver is disguised as the Gym Leader to throw you off.
 * The Pokémon Kirlia and Gardevoir can both be male despite appearing to wear a tutu and a ballroom gown, respectively (though Gen IV introduces Gardevior's Distaff Counterpart, Gallade).
 * Except male Kirlia's can still become Gardevoirs if it just evolves normally.
 * As with Gothitelle.
 * In Animal Crossing, you can wear any clothing or accessory items, even those that are obviously intended for the opposite sex. This extends in more recent versions of the game to even unlocking the ability to have girl's hairstyles or shoes on a boy or vice versa. The only thing you can't do is change the face style or actually use the opposite sex clothes model (that is, putting a dress on a boy character will make it still look like a shirt, and putting a shirt on a girl will still look like a dress)- though, this last restriction is removed in the 3DS version, which has skirts, pants, and dresses as separate kinds of items.
 * Blanca, the cat with the blank face, is evidently a male, even though "Blanca" is the feminine form, the gibber-clip is the highest-pitched one used for females, and the outfit is the female skirt. So, uh....there you go.
 * She has no name in Japan, and internationally she's been changed into a girl. Bob, another cat, is still a boy though and he wears a long floral "shirt".
 * Also, Gracie is a guy in the Japanese versions.
 * In Kira Kira, Shika is forced to cross dress against his will. Interestingly enough, despite getting more male fans than the real girls in the band, people do catch on that he's a guy through things such as the shape of his hands. He's quite relieved when he's allowed to stop not just because he was tired of getting hit on/thought of as a pervert because he was starting to get used to it. He's still a wholesome crossdresser five years later, in Curtain Call.
 * In Leisure Suit Larry III, the main character is able to dress up in a silly show-girl outfit and thus turn on a female lawyer who likes to wear masculine underwear ("I had no idea you liked cross-dressing too!") like singlets and boxer shorts.
 * Also, in ''Leisure Suit Larry 2', you need to go to great lengths to dress up as a convincing girl (getting waxed, having your hair chemically altered to become long, blonde and curly, wearing a bikini swimsuit and padding out the breasts) to bypass some KGB operatives.
 * Olivie from the Angelique series of dating sims for girls. Yes, he is a possible love interest in every game he appears in.
 * from Umineko no Naku Koro ni is implied to be this in one direction or another. Of course, because the original personality, 's, gender is never made explicit, no one's actually sure whether they're a girl crossdressing as a guy or a guy crossdressing as a girl. There's even an Epileptic Tree floating around that they're all hermaphroditic, and so in that case, they're either crossdressing all of the time or none of it. Yes, this game is confusing.
 * Death Smiles II features Lei, who is a twelve year old boy wearing an Elegant Gothic Lolita maid outfit. Apparently this is because this was the only outfit available to him when he arrived (and considering he was suffering from hypothermia, he didn't really have the luxury of being picky).
 * Mike in StarTropics crossdresses (or maybe magically changes gender) to enter an all-female village.
 * In Ike Ike! Nekketsu Hockey Bu, the Nekketsu Hockey Team can wear the uniforms of defeated rivals. Among them are an all-girl school team who wear white blouses and red plaid skirts.

Visual Novels

 * Maji De Watashi Ni Koi Shinasai has Moro who occasionally has had to suffer the indignity of crossdressing for some greater cause. Some members of the family would rather him do it more often.
 * Saber aka  from Fate/stay night. And in the Prequel Fate/Zero she dresses as a businessman.
 * Ryouta Kawara tends to show up in girls' outfits at various points in Hatoful Boyfriend. It's played mostly for laughs, since he's a pigeon. He's also the heroine's childhood friend, and considering the good ending of the "Bad Boys Love" route, he's probably her canon love interest.
 * If you follow Ryouta's path in the full version, he has a job at a transvestite cafe so he can support his ailing mother.
 * Of course, for the school festival, the heroine's class decides to be a maid cafe, so everybirdie in class dresses up as maids-- you only see the others in the full version, though.

Web Comics
"The Werewolf of London, Ontario: (on GG going incognito as a nun) And what kind of disguise is that?! Try wearing pants, that would be a disguise for you!"
 * Tip Wilkins from Skin Horse is a cheerful Casanova in a dress. He's fashion conscious and uses a variety of complex female outfits, but he makes no attempt to appear female (although given the art style, it can be a bit hard to tell). This is some kind of strange self-flagellation on part of the artist, whose previous Narbonic starred four obsessives who didn't always keep track of whether they were wearing pants.
 * Of course, it's also part of the Land of Oz motif, specifically to.
 * Magical Transvestite Cherry from Footloose, described on the cast page as "the only Magical Girl with a shred of humanity."
 * Paul "the transvestite stalker" from College Roomies from Hell!!! - granted, a bisexual prostitute and a bit of a harasser, but still a generally positive influence on the cast once he becomes a genuine character rather than a Running Gag, serving as the voice of reason essentially whenever he plays a significant role.
 * Material Girl features a teenager forced into this.
 * Maxine/Max of Art School Sub Rosa is a female who's attending Art school as a male as part of a somewhat crooked "deal" to get a scholarship.
 * Parodied in El Goonish Shive when avowed pervert (and frequent Gender Bender) Tedd is teased about trading school uniforms with Susan he vehemently protests that "I do not crossdress in women's clothing!" Susan muses that technically this is true.
 * Dana and other Elle-Boys in the Jet Dream Remix Comic always dress as females, but are fairly chaste and strictly heterosexual, apparently due to the (fictional) publisher's misguided attempt to pass the Comics Code and/or Publisher Appeal.
 * Two Kinds has Natani, who literally has a male soul after her own was magically demolished. The conflict of male mind versus female instinct is an ongoing plotline, especially in regards with Natani's relationship with Keith.
 * In Umlaut House 1 and 2 there are a few occasions where Volair and Pierce dress in drag (like father like son). Plus that one time Rick switched his prosthetic body with a female one so he could pretend to be a woman for Jake's parents. Male cheerleading captain Jack Fusselton on the other hand wears a woman's outfit as a form of psychological warfare (and unlike the other examples is straight).
 * Darren from Girls With Slingshots
 * Red Mage, the delusional Munchkin of 8-Bit Theater has a tendency to cross dress and pretend to be a woman named Deborah. He blames his father for this, but Thief states that he himself managed to put those memories into Red Mage's mind somehow.
 * Obviously, he stole them into it.
 * In the Insecticomics, the Insecticons are fond of donning Barbie dresses, and actually look quite good in them. It's hilarious. "Does this dress make me look fat, fat?"
 * Though they are Decepticons so maybe not quite so wholesome, then again they're usually too lazy to be evil and usually come off as Chaotic Neutral.
 * Toadsuke from Supah Nario Bros.
 * Green Gable from Spinnerette is the first male to inherit the costume. He hasn't bothered to change it in any way...such as by replacing the skirt with something a little manlier, or getting rid of the pigtails. Maybe he believes Real Men Wear Pink, maybe he wants to stick to tradition, or maybe he's just not all that bright.


 * It appears in Double K that nearly 90% of Kamina's plans involve putting Simon in drag.
 * In Welcome to Room 305 there's, who likes to dress up as a woman at night..

Web Original

 * In webnovel/manga Cherry Girls, everyone (probably except Yuki) is this. Nao takes it further, with the girls even treat him essentially as female and even let him change clothes in girl's dressing room without any problem, and some of them really likes him for that.
 * Leslie Audette of Flaky Pastry, who is first introduced when Marelle and Nitrine are interviewing potential roommates. The author had originally planned for the two of them to be surprised by him (i.e. "Wait, you're a guy?), but then realized that Marelle wouldn't care, and Nitrine...would care either way.
 * In the Paradise setting, humans are randomly, permanently transformed into Funny Animals (and occasionally gender-changed) by causes unknown. A Weirdness Censor renders these changes Invisible to Normals, who continue to see the Changed as their original human selves (and genders). Any gender-Changed invariably ends up a Wholesome Crossdresser, since he or she cannot dress as the gender he or she really is or it will look strange to those not in the know. Affects some changes more than others, of course, as far fewer people will find anything odd in a "woman" wearing jeans than in a "man" wearing a dress.
 * Theatrica with the character Vivian.
 * Numerous characters of the Whateley Universe, being transsexuals, dress as the opposite gender until they have the opportunity to change physical sex. Others have already done so, but choose to wear the same clothes that they always have done. Phase is a wealthy boy who looks entirely female except for the genitalia, forcing him to have custom made clothes with a masculine cut but a feminine fit except for a loose groin. Presumably many other students in Poe house, though they are not mentioned.
 * Although there is one character who is not in Poe Cottage and cross-dresses. Gotterdammerung cross-dresses because he likes it and the story that focuses on him has him unsure if he should cross-dress for Halloween.
 * Examples from That Guy With The Glasses:
 * Spoony as Spoonette and The Gate Cleaner's Wife, Linkara as 80s Chick, Benzaie as Veronique and the Critic as an Airline Hostess.
 * Critic does this fairly often and has done since he was at least thirteen, expressing much embarrassment at the home videos of a teenage him in full drag. He was also Raised as the Opposite Gender for a bit, giving him a few issues.
 * JewWario has actually crossdressed in public on several occasions (most notably at showings of Rocky Horror Picture Show).
 * Benzaie has made crossdressing a running joke on his show for sketches about his more girly interests.
 * Par for the course in any story on Literotica that's in the Transsexuals/Crossdressers section and doesn't contain either magic or bondage.

Western Animation
""Which of you is attracted to me?""
 * Bugs Bunny, when he's trying to trick someone. Most notably done in "What's Opera Doc"
 * Woody Woodpecker has done this time to time, the most memorable instances being Chew-Chew Baby, Drooler's Delight and The Woody Woodpecker Polka.
 * Pleakley in Lilo and Stitch and Lilo and Stitch: The Series.
 * Justified Trope in that having three legs pretty much rules out pants as an option.
 * And Jumba, to an extent. In the series he once dressed up as Pleakley's 'bride' and nearly married him.
 * In Rocko's Modern Life Heffer's stepbrother Peter seemed to like to wear cheerleading outfits and ballerina tutus.
 * Tutus are considered unisex nowadays, though men usually wear them for comedic purposes.
 * Timon of The Lion King ends up in a skirt in one scene ("What, you want me to dress in drag and do the hula?"), though since the animal characters don't normally wear anything it's debateable as to whether this counts.
 * In the POV Sequel, Timon was still wearing the outfit when he reunites with his Ma and Uncle Max, and they don't comment on it until after Timon has left the scene.
 * Name one Nathan Lane role that doesn't end up with him in a dress at one point or another!
 * Part of Override's bio from her toy on Transformers Cybertron (only available after entering her Cyber Key code on the TFC website) states that in order to win leadership of Speed Planet she entered the race disguised as a male. Exactly how this works (or for that matter why she'd do it) isn't mentioned.
 * It was meant as a Mythology Gag referencing the fact that in the original Japanese, she's already male.
 * Jerry from Tom and Jerry also cross-dressed a few times to trick Tom, who apparently is less likely to be violent towards a girl mouse.
 * Examples from The Fairly Odd Parents:
 * One episode has Chester dressing up as a girl so he can get a skating partner.
 * On the opposite side Trixie was a very convincing boy in The Boy Who Would Be Queen.
 * In part 3 of Wishology, Timmy's dad has been known to wear a dress with a blonde wig.
 * Stewie in Family Guy has taken to this lately. While the most prominent example is Seaon 5's "Boys Do Cry", in which he dresses as a girl to enter a beauty pageant during the Griffins' stay in Texas, he also dressed up in another episode and pretended to be Brian's girlfriend to spark jealousy on another girl.
 * Buster Bunny, usually for the same reason as Bugs, to trick people.
 * On Jimmy Two-Shoes, both Jimmy and Lucius do this while being flight attendents.
 * Jimmy ends up cross dressing frequently during the series, whether it's for disguise purposes, losing a bet or because he felt like it.
 * Both Fred and Barney of The Flintstones do this oddly often. Barney does it VERY often in the Fruity Pebbles ads, presumably just to get Fred's Pebbles.
 * Ambiguously Gay King Julien of Madagascar and The Penguins of Madagascar has worn skirts occasionally, though this may not count as he's a lemur and doesn't normally wear anything at all.

"Homer: Heh, I don't need her at all anymore!"
 * Roger from American Dad. He himself is anything but wholesome, but his frequent crossdressing is never portrayed negatively.
 * The Amazing Chan and The Chan Clan character Stanley Chan has crossdressed on more than one occasion, twice for disguises and one for the sake of being hilarious. He pulls it off quite well, too.
 * The Christmas Episode of Kids Next Door opens with the Delightful Children impersonating the Kids Next Door. The Delightful Children include one brown-skinned boy and a chubby girl, they are presumably the ones that dressed as Numbuh 5 and Numbuh 2, respectively.
 * Numbuh 5 wore a tuxedo in an early episode.
 * Several minor examples from The Simpsons:
 * Bart once demonstrated how to walk in high heels to help Lisa prepare for a beauty pageant. He was disturbingly good at it.
 * Homer and Flanders both lost a bet over a children's miniature golf tournament, forcing each to mow the other's lawn while wearing their wives' best Sunday dress.
 * In "Homer Loves Flanders", Homer fantasizes about looking at himself in a mirror wearing a wig shaped like Marge's hair.


 * In "The Springfield Connection", Homer mentions that he occasionally wears women's underwear; something that he and Marge apparently agreed was "strictly a comfort thing''.
 * Once, puppies tore up all of Bart's socks, forcing him to wear a frilly pink pair of Lisa's. He also wears pink culottes because "Hey, I gotta accessorize."
 * Unusually for a children's show (especially a Disney one), The Weekenders twice implies that Carver is a cross dresser when his friends catch him in possession of girls' clothing.
 * All Grown Up has Phil dressed as his twin sister Lil. He seems to develop a crush on another boy.

Real Life

 * Leslie Cheung. In movies like Farewell My Concubine and All's well, Ends well too
 * Just. Look. At. These!
 * David Bowie, who even in normal clothes evokes Stupid Sexy David and Even the Guys Want Him reactions, looks simply marvelous in a dress.
 * Director Ed Wood. A heterosexual transvestite (and apparently a bit of a womanizer in his younger days), he's probably one of the more famous real life examples of this trope.
 * Arguably, the entire Glam Rock movement qualified.
 * Eddie Izzard is this, and often mentions in his comedy shows that he is an "executive/action" transvestite, not a weirdo transvestite. He has also referred to himself as "a lesbian in a man's body" or "a male tomboy."
 * Several examples from the world of J Pop:
 * Mana has toned it down a little in recent years, but is still one of the most convincing crossdressers in J-rock.
 * Hizaki from Versailles.
 * Bo of An Cafe also deserves a mention.
 * Quite a few of the talents under Japanese talent agency Johnny's Jimusho cross dress often, and well enough that it has lead to quite a few amusing fan sexuality confusion moments over time.
 * TegoshiYuya IS Johnny's representative for this trope.
 * Danny Bonaduce was seduced by a cross-dresser, and found out only too late-- just as the cross-dresser likewise found out too late that Danny was a psychotic ex-child star and martial-arts/steroid freak. Bonaduce spent time in jail, and the cross-dresser spent time in the hospital.
 * Pete Burns, the English singer-songwriter, has an androgynous style.
 * Julian Eltinge was famous as a female impersonator in the early 20th Century.
 * According to one unreliable source in a sensationalist biography, J. Edgar Hoover crossdressed while participating in homosexual orgies. Skeptics of the claim say that even if he had such proclivities, it's highly unlikely that Hoover would be so reckless and indiscreet about them, which would run counter to his general personality.
 * Even the Mayor of Reykjavik qualifies!
 * Most modern Western women now wear clothes and fashions that were first popular for men to wear long before (or were unisex). This is not really a chauvinistic boast--all sorts of embarrassing things were once worn by men, such as skirts, pantyhose, stockings, high-heeled footwear, earrings, eyeshadow, perfume, etc. Some specifically form-fitting items (like brassieres) were always for women for obvious reasons. But in general, concepts of what define gender-specific or gender-neutral clothes are cultural issues that evolve over time.
 * This actually can be called a Double Standard, given that Crossdressing women seems to be looked down upon far less than a crosdressing male. A crossdressing woman might get comments of Butch Lesbian thrown at her, but a crossdressing man is likely to be seen as a Creepy Crossdresser.
 * Barry Humphries playing his character Dame Edna Everage. Just because Edna's considered "wholesome" doesn't mean she's not a massively egotistical, Stepford Smiling Grande Dame who makes Dr. Frank-N-Furter look humble by comparison.
 * Artist Marcel Duchamp went through a transvestite period as "Rrose Selavy", a genteel-looking gentlewoman type who was photographed by Duchamp's friend Man Ray.
 * Artist Grayson Perry personifies this trope. It's remarkable for him to be at a public appearance not dressed like a little girl.
 * This preschool kid.
 * Le Chevalier d'Eon.
 * Justin Bieber revealed "I’ve worn women’s jeans before because they fit me. It’s not a trend; it’s just, whatever works, works." This is more common than you might think, because most men's jean sizes start around 28", and the legs tend to be cut larger. If a man's waist size is smaller (say 26") and/or he has thin legs, women's jeans would fit better.
 * Lady Gaga. No, not just wearing pants, she actually goes full Drag King with her alter ego Jo Calderone.
 * The Men in Tutus stage production, emphasizing the ballet maneuvers that full grown men are put through over the titular tutus and tights they're put in. Yes, including the Played for Laughs moves.