Creepy Crossdresser

""How many times have I told that boy not to accept food from mortal enemies out for revenge, disguised as girls?""

- Shoubu's mother, Duel Masters

A Crossdressing character whose choice of attire is played for weirdness, for creepiness, for Squick, simply for shock value, or to show that he (and it's virtually always "he") is evil or deranged. While the look of the Wholesome Crossdresser tends to gloss over the dissonance between genders, this trope often calls attention to it. Often, this crossdresser exaggerates Tertiary Sexual Characteristics without bothering to cover up secondary (or primary) ones. Make Up Is Evil is played Up to Eleven. Frequently, the unfortunate implication is that crossdressing is, in itself, creepy, but it may simply be one aspect of a character who's generally creepy.

Japanese works tend to play up a few common traits for this character type: a combination of a gaudy outfit, a Noblewoman's Laugh and absolute narcissism. He also often has a crush on the Big Bad, The Dragon, or in more humorous works, the Chaste Hero.

Sometimes coincides with both Trans Equals Gay and Depraved Homosexual, for a lethal combination of stereotypes. May overlap with Disguised in Drag (or, very rarely, its Distaff Counterpart, Sweet Polly Oliver) if the character adopts a crossdressing disguise more often than seems strictly necessary and/or enjoys it. For the opposite, see Wholesome Crossdresser. See also Sissy Villain.

Examples:

Anime}} and Manga

 * The quintessential example of this character (in anime, at least) is Yuda, from Fist of the North Star. Outrageous outfit? Check. Annoying laugh? Check. Insanely self-absorbed and narcissistic? To eleven. Gay? Oh, boy. Just take a look at his conversations with Rei...
 * In Akazukin Chacha, Doris is the twin brother of Dorothy who is in love with their childhood friend Seravy, who has Belligerent Sexual Tension with Dorothy, ever since she had a makeover which Seravy hates (she changed her natural golden curls to a straight red-pink hair). In an effort to win Seravy's affections, he himself had a makeover to look exactly like his sister's original appearance. Naturally, this only Squicks Seravy out to the point he is usually very violent to Doris (and only to Doris.)
 * One Piece examples:
 * Mr. 2 Bon Clay of Baroque Works, the only Baroque Works officer without a female partner, since he counts as both the man and the woman. His alias reflects this, being a combination of a number (traditional for male officers) and and a reference to a holiday (traditional for female officers).
 * Taken to absurd levels with Emporio Ivankov, the "queen" of Kamabakka Kingdom. His design was modeled on no less than Dr. Frank N. Furter himself. When he was arrested and locked in Impel Down, he founded a Prisoner's Paradise between the prison's two harshest floors where everyone dressed in fishnet stockings and switched freely between genders thanks to Iva's hormone controlling "Horu-Horu" Fruit.
 * And yet despite his absurd level of creepiness, he can still be considered one of the top good guys of the entire One Piece world, being
 * Kamatari of Rurouni Kenshin, though he's portrayed fairly sympathetically and is driven by an unrequited love for Shishio. Otowa, on the other hand, is just a Psycho for Hire.
 * Jakotsu from Inuyasha. Also has a crush on Inuyasha (and flirts with Miroku and Sesshoumaru), but later is shown in a more sympathetic way through his genuine friendship with Bankotsu.
 * Supposedly, Jakotsu was originally supposed to be a woman, but the author changed it because she didn't like the idea of the characters killing a human woman, undead or not. Regardless of the gender-switch, Jakotsu is also the most psychotic and murderous of the Band of Seven, with quirks that include sadism and a tendency to torture his "lovers" to death. For example, he says Inuyasha's ears are so cute he wants to cut them off.
 * Suzu in Peacemaker Kurogane dresses in a more feminine manner after becoming gay and insane. He wears nail polish, makeup, revealing clothes, and sometimes wears a long, black fur robe (without wearing anything else underneath).
 * Fullmetal Alchemist:
 * The androgynous but genuinely male Envy has traits of this which were especially played up in the English dub, where his voice is more feminine.
 * Barry the Chopper (anime version), who dresses as a woman when out delivering meat from his butcher shop.
 * Fish Eye from Sailor Moon had shades of this, though was clearly intended to appeal to the fetish. As the other villains disguise themselves, the Hand Wave is dressing as a woman is simply a modus operandi to cover the left over type of victims - males - as Hawks Eye targeted older women and Tigers Eye targeted younger women. He actually dresses as a male for a specific mission (targeting a gay fashion designer), and while exclusively using male pronouns when in circus attire, will only use feminine pronouns when disguised. Ironically, his femininity seems to make him closer to Earth, and he has the first Heel Face Turn of the season.
 * Also Zoisite, though played a bit straighter (no pun intended) than the openly camp Fish Eye. Guilty of feminine appearance, romantic relationship with a male, shrill laugh, and sakura petals everywhere. Fits this trope because he actually crossdresses as the title heroine in order to lure Tuxedo Mask out of hiding. Though the crossdressing was Kunzite's idea, not his.
 * Zoisite and Nephrite both crossdress to disguise themselves in the manga. Also, it is not Fish Eye but Hawks Eye who crossdresses in the manga.
 * Elendira the Crimson Nail from Trigun Maximum (the later volumes of the manga), although he or she is most likely a Transsexual woman.
 * Given the body-mod capabilities of Gunsmoke science demonstrated in the series, she could be, but could also still be male. Either way, she's scary as hell, one-upped Legato by some way, but was sadly too freaky (as much for the 'fighting style based on graphic impalement with giant red hardware from nowhere' bit as for the transexuality) to get into the anime.
 * Despite the nice wide shoulders, this troper would probably never have taken Elendria for anything but a woman, had not the first comment made by anyone after she dropped out of the sky for the first time been Meryl's 'A...transvestite? It has a nice figure...' and Wolfwood's later 'A guy like you...' [Elendria gives him a look.] 'A woman like you...'
 * Notable for the fact that, unlike Kamatari above, although she's competing for the affection of a man who will never look at her she's easily the most sane and the most physically powerful force he can mobilize, until he  (Meanwhile Legato's 'eat steak with no hands' and 'float around in sarcophagus of doom' lines have inspired mutinies out of sheer embarrassment from his subordinatees.
 * Can we get Freudian about those humongous nails ramming through bodies, please?
 * The Big Cheese from Samurai Pizza Cats. Strangely, his flirting with male subordinates was mostly left intact.
 * Lady Bat from Mermaid Melody Pichi Pichi Pitch
 * McCoy from the anime Bakuen Campus Guardress is a semi-subversion of this trope. He has the laugh, the mascara and the leather dominatrix outfit, he brags about how beautiful he is.... and he is built like a linebacker.
 * Orochimaru of Naruto, who is actually a man in a woman's body (by the start of the series) Shapeshifting as an effeminate male. Just to make matters creepier, he first shows up wearing a woman's face as a disguise, after tearing it off her body.
 * Made even worse in an omake where he and his apprentice, Kabuto, show up... wearing Sailor Fuku. UGAH!
 * Flame of Recca's Kurenai may be effeminate, but the real version of the trope doesn't appear until very late in the manga when the clone Aoi poses as a female student. Recca seems nonplussed considering the much stranger people he's met at this point, except in being completely confused by the reformed Aoi trying to explain his complicated backstory.
 * Monster offers a particularly creepy example in which this trope is not played for laughs.
 * Bleach
 * Luppi, the briefly Sexta Espada. Note however that the Arrancar Robe seems to be rather "unisex". Not that it does make him any better...
 * Also Barragan's Fraccion, Charlotte Cuulhorne.
 * Pokémon loves crossdressing villains:
 * Team Rocket, most of the time: Jessie would crossdress as a male (complete with mustache), while James crossdressed as a female at the same time. No reason was given why they couldn't just disguise themselves as their own gender.
 * Perhaps the most disturbing example is the infamous "bikini contest" episode. I'll just leave it at that.
 * Harley is also a great, albeit much less permanent, example, but technically he only crossdresses once.
 * The members of the Zuka Club in Ouran High School Host Club. The crossdressing is justified by the club being a blatant parody of the Takarazuka all-female acting troupe, where both male and female parts are played by women.
 * Jo Jos Bizarre Adventure
 * Diavolo, the Big Bad in Part 5 straddles dangerously close to this with both of his personalities.
 * Annasui might classify as this depending on who you ask, given his Heroic Sociopath nature. But he is technically part of the "good guys", so he might be in a different category of crossdresser.
 * Code Geass examples:
 * Earl Kanon Maldini, the aide to Prince Schneizel. In the series, he is not shown as a crossdresser (but he is feminine looking enough and once jokes about aiding Schneizel in "his private affairs" as well), but the Code Geass novels not only say he is, but that he was persecuted for it until he met Schneizel and was hired as his assistant.
 * Lelouch does this at least twice in the picture dramas. In one of them, the Student Council has a crossdressing festival so everyone crossdresses (and Suzaku... mentions having done it a few times before?). And he looks REALLY good in girl clothing.
 * Tsubasa Kurenai from Ranma 1/2. A straight guy who dresses up like a schoolgirl and relentlessly stalks former schoolmate Ukyo Kuonji (a straight girl who spent most of her life dressing up like a guy) while disguised as various inanimate objects. Tsubasa is assumed to be a lesbian at first because he's very passable and is only interested in women. Ranma tries dating Tsubasa while in male form to set "her" straight, only to find that Tsubasa is a boy.
 * Mariya from Maria Holic does a very convincing job as a girl. Since this is an all girls' school, no surprise that he gets Kanako falling for him the moment they meet. He's also incredibly sadistic.
 * One early example of this trope would be Rock, from the various manga by Osamu Tezuka. Who, in his more villainous incarnations, would often disguise himself as a woman.
 * Yuuji Fukunaga from Liar Game starts off as this, but slowly pulls a Heel Face Turn and becomes one of the main supporting characters while still making a better looking girl than most of the female cast combined.
 * Magical Girl Lyrical Nanoha has the.
 * The Kirby anime has Escargon, a Camp Gay villain with a not-so-subtle crush on his boss who has crossdressed a few times (usually because said boss wanted him to).
 * Fumiya Ninomiya from Wandering Son crossdresses just to impress Saori Chiba. While not an outright "villain", he is portrayed as a bit of a slimeball when compared to the actual transsexuals.
 * Ghost in the Shell:Stand Alone Complex has a special case in which  Pycho Ex Girlfriend wants to kill him and take both his cybernetic body and his identity.
 * from Sakura Gari
 * Rosiel from Angel Sanctuary often skirts the line with his... unusual outfits. Anti-Villain Belial also counts.
 * Played for Drama with  and.
 * Chapter 279 of Air Gear reveals that the villainous loli Shalott who dresses in a frilly dress and wears a Nice Hat is actually a guy.
 * Hansel and Gretel of Black Lagoon are very fond of swapping clothes (and, more disturbingly, personalities) with each other. Which one's which gender, though, is anyone's guess.
 * Black Butler: In episode five of the second season, Alois Trancy dresses up as a maid to lure Ciel into his bedroom so he can flirt with him and take his eyepatch. It's also shown that he has a few dresses in his wardrobe.
 * "Miss Aki," an unattractive example from Abenobashi Mahou Shoutengai
 * Count D in Pet Shop of Horrors is good friends with a group of drag queens and transvestites, and his peacocks also appear this way in their 'human' forms.
 * One of the bad guys in one of Lupin III OVA was Herr Maphrodite, who doubles as a Sissy Villain. He's clearly homosexual too, since he clearly dislikes Fujiko's presence.
 * In the manga of Jungle wa Itsumo Hale Nochi Guu, Bel is a crazy heterosexual crossdresser. While sometimes shown looking normal in menswear, when in drag, he always covers his neck and flat chest so no one notices the lack of boobs or the Adam's apple.
 * Michio Yuki of manga series, MW, cross-dresses as his female victims after killing them.

Comic Books

 * The Purple Marauder, transvestite women-hating archnemesis of the Anti-Hero Lusiphur, the elvish protagonist of the series Poison Elves (originally titled "I, Lusiphur") by late artist/writer Drew Hayes (1969-2007). The Purple Marauder (a human) is a foppish Zorro-like vigilante swordsman who terrorizes the world of Amrahly'nn with his rapier and mustache-twirling villainy but mainly with the sight of his hairy fishnet-clad legs. He dresses, as the name insinuates, all in purple from head to toe: large purple hat, purple women's dress, purple boots. His sworn mission: To convert men from the ways of lust and women.
 * While he's technically more of a mercenary with a small modicum of heart and it was only the once, when Deadpool spent a brief time with the X-men he insisted on wearing one of their costumes. Specifically, Marvel Girl's. For unknown reasons he also retained the underwear from the costume underneath his suit even when he went back to his black-and-red tights.
 * In Grant Morrison's Arkham Asylum: A Serious House on Serious Earth, the Joker was originally going to be sporting a costume with Madonna's signature cone-shaped bra and stilletto boots, simply because he knew some people find crossdressing morally objectionable.

Film
"Ace Ventura: "Einhorn is Finkle...Finkle is Einhorn! Einhorn is a man! Oh, my god! Einhorn is a man?!"/"
 * Dr. Frank N. Furter from The Rocky Horror Show. Also a Depraved Bisexual, not that anyone's complaining.
 * Buffalo Bill from The Silence of the Lambs. He seems to be an erotic crossdresser who's expressed interest in sex-reassignment surgery. Dr. Lecter and Clarice agree that he's not really transgender.
 * Ace Ventura: Pet Detective: The titular detective gets particularly grossed out when he learns that the "woman" he kissed earlier in the film is actually a guy who had stolen the identity of a missing hiker.

""Despite his stupid name, I have to admit that Dark can be a pretty interesting character. Until this point in the movie we never actually see him. When he walks onscreen, however, he steals the show, mostly because he is wearing women's clothing. Without explanation. When you see a cross-dressing serial killer in a movie, he is usually wearing makeup in a dress. Something that says "hey, I am a psycho and I wear clothes that obviously belong to a woman." This is not the case with Dark. Instead of a skirt or something, he wears a pink tube-top and woman's executive jacket with padded shoulders. And, again, this is never explained. It is almost as if the movie goes out of its way to ignore this fact, like the only person who would take the role was some cross-dresser at the bus stop and they're trying to downplay the fact.""
 * Pretty much everybody else (yes, even the dolphin) is just as grossed out when Ace reveals it, in fact.
 * In Beyond the Valley of the Dolls, the character
 * Even James Bond's nemesis Blofeld undertook a spot of cross-dressing (although it was technically a desperate disguise) in the film adaption of Diamonds Are Forever. Also, Thunderball has an old enemy of Bond disguised as his own "widow".
 * Michael Caine in Dressed To Kill.
 * In The Dark Knight, The Joker disguises himself as a nurse in one scene to get to Harvey in the hospital. Instead of wearing unisex scrubs or just dressing as a male nurse, he goes drag, complete with a wig. It manages to be funny and creepy at the same time. (Don't forget erotic!)
 * It was likewise intentionally invoked, seeing as he'd kept his Joker facepaint and green haircolor.
 * Freebie and the Bean, a buddy cop film from the 70's, features a beautiful blond crossdressing antagonist played by Christopher Morley.
 * After the climax of Alvinandthe Chipmunks: The Squeakquel, Ian Hawke tries to stand in for the Chipettes after he lost them, failing spectacularly.
 * in Terror Firmer.
 * Leatherface is a crossdresser in Texas Chainsaw Massacre the Next Generation. The character was loosely based on real-life killer Ed Gein (listed below) in the first place anyway, so it makes at least some kind of sense, unlike the rest of the movie.
 * Norman Bates from Psycho.
 * Both Frank Booth and Ben, two villains from Blue Velvet, deserve some mention here as they both wear feminine makeup at some point in the movie.
 * In Death Wish V:The Face Of Death one of the villains is Fredrick "Freddie Flakes" Garrity (not at all played by Sid the coroner from ["CSI: NY"]), a high-priced mob assassin (nicknamed because of his frequent dandruff) who not only crossdresses during one of his schemes, but later, when hanging out with his girlfriend, comments her shoes, saying he can't wait to see how they fit. (He also has what is quite possibly the stupidest death of the series, immolated by an exploding soccer ball).
 * Belle in Fright Night Part II. Paired with some rollerskates, he's (she's) definitely Our Vampires Are Different.
 * Deconstructed and Played for Laughs in Austin Powers: International Man Of Mystery. Austin is used to spotting and de-wigging evil assassins disguised as women, as befitting a Campy Tuxedo and Martini spy flick, essentially rendering him Wrong Genre Savvy in The Nineties. This leads to him knocking back Basil's poor mother and trying to pull her wig off.
 * Boondock Saints - Detective Smecker (William Dafoe) gets a little too into character when dressing drag to infiltrate a mob manor. So do the Mook guards.
 * Bob, one of Holli Would's Goons from Cool World.
 * Zack from the 1988 Slasher Movie Hide And Go Shriek.
 * Dark from 2002's Hunting Humans. As Something Awful put it:


 * Marion Penrose in Unhinged, due to his mother being an insane misandrist.
 * The villain of the Hong Kong slasher film He Lives By Night is a crossdressing serial killer who prowls the streets at night, brutalizing women before strangling them with white stockings.

Literature
"Nobby: Do I look good in taffeta?
 * "Why Grandma, what big eyes you've got!" The Big Bad Wolf from Little Red Riding Hood is one of the oldest ones in the book, dressing up as the title heroine's grandmother.
 * Norman Bates from Psycho.
 * Norman doesn't really fit the stereotype given in the trope description-- his cross-dressing is to give his other personality a more convincing appearance.
 * In the Redwall series, Emperor Ublaz Mad Eyes is a possibly-not-intentional-on-the-author's-part borderline example. The silk robes, painted nails and perfume he is mentioned as having in his first appearance are par for the course for an evil exotic emperor, but the entire book revolves around him attempting to steal a famous set of six large pink pearls to put in his crown. He goes so far as to slaughter entire tribes to get the things. He also stops in the middle of his angry Mirror Monologue to debate what he's going to wear for the victory parade; "If I had the Tears of all Oceans now, they would be set in my crown, all six of them, wondrous rose-colored pearls! I would don my green silk mantle, or maybe the black one with gold trim ..."
 * An odd little novel called Pest Control by Bill Fitzhugh featured, among other things, a diminutive hitman who likes to dress up as a little girl to do his hits. He also bangs a repressed middle-aged mom who has a thing for midgets and circus peanuts.
 * "Adult comics" vendor Sid Sleaze in Who Censored Roger Rabbit? (Literature)?
 * Antiheroic example in Discworld's Nobby, who picked up the habit in Foreignland and has gotten to the point where he asks:

Angua: Erm, yes. Lovely.

Nobby: Really? You don't think it makes me look too fat?"


 * Herman Goering was depicted as a transvestite in A.E. Hotchner's novel The Man Who Lived at the Ritz.
 * Bèbelle from Malevil. Part of it is being creepy and evil, another part is using Disguised in Drag to infiltrate settlements prior to his marauding army invading.

Live Action TV
"Rimmer appears in an observation window. He is NOT in uniform.
 * Borderline-ish example: the second season of Skins features a character who, while still visibly female, binds her chest and dresses in boyish clothes with hopes of making herself more attractive to the object of her romantic obsession, who happens to be gay. It doesn't work.
 * Alonzo Torquemada of HBO's Oz is a tall, strapping Hispanic crossdresser with one glass eye and a penchant for hallucinogens. While not quite as evil as his namesake, Torquemada isn't above slipping his enemies poisoned dope, or seducing Miguel Alvarez.
 * When Luke and Laura on General Hospital went on the run in 1980, they eventually encountered Sally, a hitman who wore a dress.
 * The episode "Machismo" of Criminal Minds was Ripped from the Headlines about Mataviejitas, "The Old Lady Killer." It featured a man who dressed as a woman to gain entrance into old elderly women's apartments to kill them. The actual case is a subversion. Authorities believed the killer was a man dressing as a woman; in fact, she was just a woman. It's worth pointing out that the show lampshades and (perhaps?) subverts the trope, explicitly stating that their villain is not a crossdresser: dressing as a woman is not a lifestyle for him, but a tactic.
 * It may have actually been more than a tactic. Before he became a serial killer, he was a serial rapist, and even then he wore dresses and the like, despite having no apparent reason to (he didn't use a ruse then, just blitzed the victims, who never really saw him, since he came up from behind and blindfolded them).
 * The UnSub in "Limelight" is a crossdresser, wearing his victim's clothes as a means of reliving his murders.
 * "Conflicted" takes the cake of this trope, with an UnSub who is a cross-dressing serial killer alter personality who lures and disarms her victims sexually and then rapes them (penetratively). The cross-dressing is more convincing to the characters than to the audience, and to top it off, the UnSub has a habit of suddenly cross-acting without redressing.
 * While The Master spends the majority of the Doctor Who story The End of Time wearing a black hoodie, the climatic sequence where
 * Real Life head of the Nazi Luftwaffe Herman Goering was depicted as a transvestite in a 1988 TV Movie, The Man Who Lived at the Ritz, based on A.E. Hotchner's novel.
 * Red Dwarf plays this Trope for laughs a few times:
 * In the season five episode "Demons and Angels," Lister is running for his life from the evil versions of the Red Dwarf crew, until he runs into Evil Rimmer ... wearing what's best described as a Dominatrix-type get up.
 * In another Series 5 episode, "Quarantine". When Rimmer contracts a holo-virus that sends him mad, he appears out of uniform, and holding Mr Flibbles. Also lampshaded:

Rimmer: Is something amiss?

Lister, trying to disguise the tremor in his voice: Amiss? God no. What could possibly be amiss?

Rimmer: You don't think there's anything amiss? I'm sitting here wearing a red and white checked gingham dress -- and army boots -- and you think that's un-amiss?"

"Narrator: It was the exact plot of Mrs. Doubtfire."
 * Dean Pelton of Community could be considered a Wholesome Crossdresser, as he's not a bad guy, but pretty much everybody is weirded out by his bizarre (that at times could reveal a bit too much) outfits, which puts him in the territory of this trope. It doesn't help that he's also a dalmatian furry fetishist with a serious crush on one of his students.
 * Arrested Development has a few:
 * Tobias would be "wholesome" in his motivation, but the results creep out pretty much everybody:
 * After Lindsey kicks him out, several episodes have Tobias dressing as an elderly British nanny so he can stay close to his daughter.


 * In an effort to help Buster overcome his low self-esteem and be more assertive with his mother, Tobias dresses up in Lucille's clothes; including her underwear. It doesn't even make sense in context.
 * Barry Zuckerkorn goes to the City of Industry to pick up a prostitute, but quickly drives off when the prostitute reveals that she is not a man in drag. There are also some hints that Barry himself is a closet cross dresser.
 * While he was hiding in the attic, George Sr. dresses in his late daughter-in-law's maternity clothes. During a hug, Michael also notes that he was wearing her perfume, too.

Music

 * The titular character in Pink Floyd's first single, "Arnold Layne."
 * The Velvet Underground's "Sister Ray".

Newspaper Comics

 * Sanjak from Terry and the Pirates is a rare female version.

Professional Wrestling

 * Harvey Whippleman as "Harvina" won the WWF Women's Championship, and Santino Marella's identical twin sister "Santina" won the Miss Wrestlemania battle royale.

Theater

 * The Rocky Horror Show.

Video Games

 * Kefka is the only male character other than Cloud who is allowed to wear the crossdressing items in Dissidia Final Fantasy. Then again, given that in the same game his official preferred weapons are flutes this might be an invocation of the Rule of Funny.
 * Flea from Chrono Trigger. A popular fan theory that made it into some fanfic was Flea, being from a race of monsters, doesn't worry about the details of what humans wear so much as wear what he thinks is cute.
 * This may not quite excuse the official art having a bust.
 * Padded outfit. You can even get the item in-game, can't you?
 * "She" is a cutie in the sequel, though.
 * Chrono Crossdresser?
 * Another notable game example is the villain Alfred Ashford, from Resident Evil: Code Veronica. He not only dresses in drag to pose as his own sister, but has an irritatingly mincing laugh and an extreme hatred towards the female protagonist, Claire.
 * Plus, he has an obsession for the Big Bad that could be taken as a crush, despite the fact that.
 * The SNK Gals Fighters Fighting Game has "Miss X", who is essentially the Badass Iori Yagami in a sailor uniform and a bandit's mask. Predictably, no one in the rest of the all-female cast falls for it, and all of them point it out immediately.
 * Gao from Rhapsody a Musical Adventure. In fact, due no doubt in large part to the graphical limitations of the game, it's actually near-impossible to tell it's a girl. She ends up giving a forced, out of place speech about how people can't tell she's a girl just before you fight her simply so the audience can know.
 * Ganbare Goemon is rife with these, the most prevalent being Sister Bismaru, Ebisumaru's descendant who dresses like a cross between a nun and a miko.
 * Super Mario Brothers: Birdo...at least in Japan.
 * "His" laying eggs from his mouth just makes it wierder.
 * Justice from Guilty Gear counts, if only because of the huge crotch spike in her armor ...
 * There's also the tendency for people to identify mecha as male unless they look distinctly feminine. Even without the crotch spike, she looks sort-of gender-neutral, and thus would likely be identified as male at first glance.
 * More obviously, Testament in the first game, which also doubles as the game where his gender is the most ambiguous (thanks to him practicing his Voice of the Legion.) Later games make his gender more obvious and his change in allegiance make him more of a Wholesome Crossdresser.
 * Kanan of Soul Nomad and The World Eaters, according to Vitali. counts as well.
 * Final Fantasy Tactics a 2: The Night Dancer is a cross-dressing Camp Gay Bangaa. He even wears lipstick (on a Bangaa!) and eyeshadow and refers to himself as female, but fights with him tend to be fought under the "No harming the opposite sex" law, which outs him as male by the fact that female characters attacking him break the law while male characters attacking him do not. (On the other hand, some are so convinced by his insistent female identification that they really believe that he's a she and the law identification is a bug.)
 * In Black Sigil: Blade of the Exiled,.
 * A man in Fable II is wearing a very crude attempt at a home-made woman's outfit. It turns out that he's insane and trying to feed people to his adopted family of goblin-like monsters. The game allows the player character to cross-dress, but no other characters do.
 * Either Zepar or Furfur from Umineko no Naku Koro ni. One is female and one is male, but as for which is which...
 * In Saints Row 2 the player can dress their character in any clothes in the game, regardless of gender. So the player can make their character a transvestite, or even a Transsexual through Easy Sex Change, if they so desire.
 * The Medic in Team Fortress 2, sort of. He has an unlockable wig that's in a geisha style with a comb and small flowers, leading to a Broken Base over those who thought Valve was pandering to the fans who wanted more Ho Yay (not all crossdressers are gay and not all gays crossdress, guys). If you know your history, geishas were originally all male. Regardless, it's a compliment. It's a Shogun: Total War-inspired item, and geisha are some of the most badass units in that game.
 * in Deadly Premonition, who at that point in the story has been in such a massive Trauma Conga Line as well as that he's gone completely off the edge of sanity.

Web Comics

 * Last Res0rt's Kurt Striaeta is not-so-ironically nicknamed "Geisha" and shown in his mugshot wearing a very feminine kimono. The surprising part is, he's actually one of the few "explicitly evil" criminals in the comic.
 * of Concession is not technically a villain, but is definitely problematic.
 * Nicholas in Samurai Princess has a very serious case of a bad man trying to be a woman. He has so far been shown in a geisha-like dress, a catsuit and, heaven forbid, a maid outfit.
 * Red Mage from Eight Bit Theater often wears a dress for not always apparent reasons.

Web Original

 * In Survival of the Fittest v2, Damien Carter-Madison comes across women's clothing inside a wardrobe... and starts playing dress-up. One of the outfits he tries on is a sailor fuku, of all things. Note that he is a well-known villain of that version.

Western Animation
""Oh well, I suppose it does make me look pretty.""
 * The Star Wars: Clone Wars movie gives us Ziro the Hutt, a Camp Gay space slug with the mannerisms of Truman Capote, who tries to murder baby Stinky the Hutt. Although the Hutts are hermaphrodites according to the Expanded Universe, Ziro is Stinky's "uncle".
 * The Devil-analog Him from Powerpuff Girls usually dresses in a fuzzy pink skirt and thigh-high stilleto boots. His voice also tends to shift between falsetto and a deep growl depending on his mood.
 * Sakko from Super Robot Monkey Team Hyperforce Go!.
 * Ice Man, of all characters, has a go at this in the beginning of the Mega Man episode "Ice Age".
 * In The Fairly Odd Parents, Timmy managed to humiliate Crocker on a global scale and get him arrested for developing a supposed computer virus by uploading a video file of himself modeling one of his mother's dresses.

": You, uh, probably shouldn't tell Heloise about this.
 * Played for Laughs in Jimmy Two-Shoes, during a Zombie Apocalypse, Jimmy sees Heloise about to consume what will turn her into a zombie. However, when she turns around, it's mose definitly not Heloise.

Jimmy: Really, I wouldn't know how."


 * In Western Animation The Simpsons, episode "There is Something About Marrying", pro golfer Veronica was going to marry Patty under the false pretense of being a lesbian woman. (It's somewhat unclear, but Veronica doesn't seem to be a genuine Transsexual so much as a creepy male golfer who only crossdresses so that he can compete on the womens' tour.)

Real Life

 * Herman Goering, Nazi head of the Luftwaffe, is sometimes referred to as a crossdresser or transvestite, but there seems to be little to no substantiation of this notion. He was clearly fond of dressing up - in ostentatious (even by Nazi Germany standards) military uniforms. Some fictional portrayals of Goering depict him as a crossdresser (see above.)
 * Murderer Ed Gein is often described as this trope, and one who didn't stop at just the clothes. But while this is the most common interpretation of Gein, it's also a sensationalistic one. His psychiatric assessments hold instead that he wanted a replacement for his mother, one he could keep around.
 * The drag queens/transvestites who attacked a McDonalds in 2007. After removing their earrings and stiletto boots, of course.
 * In Ancient Rome Publius Clodius Pulcher dressed up as a woman so that he could sneak into the Bona Dea festival (a sacred religious rite strictly confined to women) and seduce the wife of Julius Caesar. He was caught when a servant tried to encourage the seemingly shy "girl" to join in the festivities; Clodius' masculine voice gave him away and he was chased out of the house by Caesar's mother. He was brought to trial for sacrilege and indecency but managed to escape conviction by bribing the jury.
 * Subverted with the serial killer Mataviejitas, "The Old Lady Killer," who the Mexican police were convinced was a transvestite because people said they saw a large muscular woman leave the houses of the victims. The police (after finally admitting there was a serial killer) ran a dragnet through the transvestite community to find her. It turns out the killer was female, Juana Barraza, a Mexican Indy wrestler known as La Dama del Silencio, the silent lady. This did not stop Criminal Minds from playing this trope straight when they did this case.
 * Sam Duddy, a senior UDA/UFF figure [Northern Ireland Loyalist terrorists] who died in 2007, once worked as a drag queen under the name Samantha. He was once a suspect in the murder of Pat Finucane, the Roman Catholic lawyer shot dead by the UDA in 1989.
 * Peter Langan, the leader of the "Aryan Republican Army," a group implicated in the Timothy McVeigh bombing, was discovered to be a crossdresser, going out at night dressed up as a woman.
 * Canadian Col. Russell Williams, who is as of October 2010 being sentenced for multiple murders, sexual assaults, breaking and entering, and so on, took thousands of photos documenting his crimes. Newspapers often put the ones of him wearing little girl's underwear on their front pages to demonstrate his depravity.
 * The general legacy of FBI director J. Edgar Hoover is about as controversial as his supposed crossdressing. In truth, it's extremely unlikely that he belongs either in this trope or Wholesome Crossdresser, but the notion has become Common Knowledge.
 * In Afghanistan, weapon smugglers sometimes wear burqas to conceal the goods.