Disguised in Drag



"Sirrah, go you to Barthol'mew my page, And see him dress'd in all suits like a lady; That done, conduct him to the drunkard's chamber, And call him 'madam,' do him obeisance."

- Lord, The Taming of the Shrew

Any scenario where a man dresses as a woman for purposes of disguise. In many cases, this results in a Paper-Thin Disguise, the male character with his square jaw and broad shoulders looking like an Amazon at best and a Drag Queen at worst... but it's still good enough to fool others most of the time. He may look genuinely attractive as a woman, but Attractive Bent Gender is likely to come into play in either case.

Frequently, but not invariably, Played for Laughs. May result in An Aesop about walking a mile in women's shoes.

Subtrope of Cross Dresser. If the character wears female disguises more often than seems strictly necessary and/or seems to like it to some degree, then he also qualifies as a Wholesome Crossdresser or Creepy Crossdresser.

Sweet Polly Oliver is the Distaff Counterpart of this trope, but is more likely to be Played for Drama.

Harmless Lady Disguise is a subtrope.

Advertising
""Woman" #2: seeing a man making goo-goo eyes at "Woman" #1) Isn't that Ed from accounting?"
 * In a series of commercials for Bud Light a bunch of guys dress as women to take advantage of Ladies' Night at a bar, where Bud Light is for sale at a reduced price for women. To (almost) everyone it's obvious that they're really men.

Anime and Manga
"Rinne: 'How do I look?' Tsubasa: 'How am I supposed to answer that?'"
 * Mazinger Z: Done by -- of all people! -- Baron Ashura at least twice (in episodes 7 and 36). He/she disguised like a woman to manipulate a mob or frighten nosy people away one of his/her operations. Fortunately he/she was a shape-shifter, so it was not so hard looking like a woman how it would be to him/her (on the grounds of Ashura being half-male, half-female). It overlapped with Creepy Crossdresser since it was pretty squicky -and eerie-.
 * Code Geass had three male characters do this in one of the picture tracks. We had [[media:Yhlothere.jpg|Rivalz and Suzaku]], but also [[media:Luluko.jpg|Lelouch]]. In a later one, Lelouch was forced into a bridal dress. This scene was then added into the visual novel game Code Geass: Lost Colors. It was truly hilarious, considering he makes a rather attractive woman.
 * Suzaku does it Lost Colors again as well, though it's not quite as attractive, or convincing.
 * This is the premise of I, My, Me! Strawberry Eggs, wherein the protagonist dresses as a woman to teach at a school run by a misandric headmistress.
 * A major plot element in the first half of the unusually good Turn a Gundam, where the protagonist Loran is put into situations where he is forced to cross dress in order to become the Gundam's "alleged" pilot Laura. This is addressed directly in the last episode when one character asks Guin (the man who made everyone think Loran was a woman) why doesn't he just put him in a skirt himself.
 * Also happens to in Mobile Suit Gundam 00, when he must infiltrate a high-class party. The thing is, he's androgynous enough to totally pull it off; anyone who didn't know his true sex would be utterly fooled. He rationalizes it as a good disguise because all Gundam Meisters are known to be male, but Wang Liu Mei (and the viewers) guesses that Sumeragi was having a bit of fun at his expense.
 * It's a Running Gag in Ranma ½ that, whenever Ranma turns into a girl and dons a Paper-Thin Disguise (which is often little more than a Wig, Dress, Accent or a cheap pair of glasses,) his rival Ryoga will invariably fall for it, and think of "her" as a very cute girl. Not only that, but both in the anime and manga versions of his introduction, Ryoga expressed his outrage over the fact that Jusenkyo turned Ranma into a beautiful girl, whereas he was turned into a small black piglet.
 * In order to distract the Orochi, a giant pervert who loves girls (to look at as much as to eat,) Ranma, Ryouga, Shinnosuke, and Shinnosuke's Grandpa crossdress as Fetish Fuel Station Attendants (namely, a schoolgirl, a nurse, a policewoman, and a bride.) The funniest part is that Ranma does this as a man (of course, had he done it as a woman, the Orochi would've made a beeline for her.)
 * Inverted and played straight in the manga Wandering Son. Played straight with male protagonist Shuuichi Niitori's wishing to be a girl to the point he begins dressing as one. Inverted with his best friend Yoshino Takatsuki, a girl who takes up dressing as a boy for exactly the same reason.
 * In Slayers, the heroes have to go to a Holy City where priestesses are trained and all permanent residents are female. They get involved with the ruler's child who does not want to be a priestess and is in fact male and forced to crossdress by his overbearing mother. At the end it is revealed that the "all-female community" is in fact fifty percent male.
 * Gourry also has to disguise himself as a woman in a couple other episodes (always episode 17 of the season). Only Evolution-R averts this tradition, being a BLAM Episode instead.
 * In one episode of Yu-Gi-Oh 5D's, Lua disguises himself as his twin sister Luca to enter a tournament because she doesn't want to enter and he wasn't invited. Once he actually gets onto the field he doesn't even bother acting like a girl, except to pretend very badly when his opponent points out that he's a boy.
 * In the first season of the Pokémon anime, Ash had to disguise himself as a girl to gain access into the Celedon City Gym, as he had offended Erika, the Gym Leader, earlier in the episode. It went on to become a Running Gag Once a Season.
 * If Team Rocket uses a disguise that involves a female and a male role, James will almost always dress as the female. (And very lovely he looks too.)
 * In D.N.Angel, Satoshi disguises himself as a woman in order to distract Handsome Lech Dark during a heist. It works -- he nearly kisses Satoshi before he realizes who he's talking to, and at that point Satoshi had already handcuffed him to the wall.
 * In a manga-only part of Fushigi Yuugi (and a series of short segments after some of the anime OAVs), the Suzaku warriors wash up on the shores of a matriarchal society after shipwrecking, and are forced to pass as women. Played for high hilarity when Gentle Giant Mitsukake reveals himself as a woman, only for it to be digitally pixelated out because it's too horrible to look at. More hilarity is mined when Chichiri turns himself into an adorably gorgeous young woman, prompting a jealous reaction from Nuriko, who's been crossdressing since the beginning of the series and is horrified that someone might make a prettier woman than him.
 * Hare from Haré+Guu was disguised as a girl once.
 * Train from Black Cat has this happen to him in the anime. Also coupled with him turning into a cute little boy (due to being shot with a Lucifer bullet). Due to him shrinking in size, no one else except Eve has clothes his size - so he ends up having to wear her dress temporarily. The saddest part? He looked damn good in it.
 * And Sven, also in the anime. Y'see, they needed bait to lure out a Serial Killer who preferred to target women, and Sven's chivalrous attitude just wouldn't allow him to let Eve do it, so... Averted in the manga, where he did let Eve do it, reluctantly.
 * Harukanaru Toki no Naka de - Hachiyou Shou has an episode where the main group is trying to help a young couple, and comes up with a plan that involves impersonating them. When the option of Akane playing the role of the girl gets rejected for being dangerous, Eisen suggests that one of the Hachiyou could dress as a woman... and everyone immediately agrees that he is perfect for this task. (Eisen should have accounted for the fact that he is pretty enough to pass as a girl without much effort; the man they were trying to fool even offers "her" to become his wife upon discovering that "she" is not the princess he was searching for, but a different girl...)
 * In the GetBackers manga, this is one of Ban's *ahem* genius plans to try to get them into a prison. He has both him and Ginji dress in school girl uniforms and try to pretend that they're on a field trip and want to visit the prison. It doesn't work. Though they actually do look quite cute in it...
 * Although not normally used as a disguise, Hermione Ayasaki is once used as such in an alternate story, to keep Hayate from being killed and Izumi from getting in trouble for having a boy in her room from her father. 'She' is hired as a maid by said father, though the other characters see through the disguise easily, as is normal for Paper Thin Disguises within the series.
 * In El Hazard, Makoto, the male hero, happens to look just like the missing princess of the magical land the characters visit. The royal family forces him to impersonate her. That created a very uncomfortable moment with the princess' lesbian consort.
 * In Otome wa Boku ni Koishiteru, the main character spends most of the series in this kind of disguise--that is, he passes for several months at an all-girls' school, despite being found out more than once.
 * A plot point for episode 4 of Black Butler. And one guess who got dragged into the drag. Give up? Ciel.
 * And in season two we have Alois briefly disguising himself as a maid.
 * In RIN-NE, Rinne decides to dress in a maid uniform to try and capture a damashigami who is kidnapping school girls. It works. He actually has to unmask himself as male to his opponent when he defeats him. He then takes advantage of his situation to win the school's Mr. Lady competition. While Sakura and her female friends agree he looks cute, Tsubasa is at a loss for words.

"Germany, Germany! I was hitting on someone because I thought it was a cute girl, but it was actually France in disguise!"
 * In Wild Rock, because Yuuen is an incompetent huntsman and a bit of a runt his father gets him to dress up as a women for a Honey Trap ploy to get more food.
 * France from Axis Powers Hetalia once dressed up as a girl to capture Italy. The plan is pulled off without a hitch.


 * In the Yu Yu Hakusho manga, Yusuke pulled this off pretty well and look like quite a convincing girl believe it or not.
 * Conan Edogawa and Kaitou Kid have both shown no issues with disguising themselves as girls when it helps their current plans. The first case that includes Kaitou is both squicky and funny since
 * Edward Elric himself from Fullmetal Alchemist has disguised himself as a girl only once in the first anime. Whether or not that was successful would be difficult to say.
 * There's one scene in episode 7 of Fractale where Clain Necran does this while roaming a city populated by Doppels.
 * During the yuki-onna arc of Rosario + Vampire, Tsukune has to disguise himself as a girl to get into the coming of age ceremony, where men aren't allowed.
 * Unsurprisingly pulled off by Alto Saotome in Macross Frontier Sayonara no Tsubasa where he.
 * In Pandora Hearts retrace 48 Oz briefly disguises himself as a maid with Alice. And looked damn good in it. Gil even says he looks gorgeous.
 * In the novel, Oz and Break were disguised as noblewomen in an attempt to ruin Gil's date with a woman.
 * Lupin III does this fairly often, often disguising himself as a female ally (such as Femme Fatale Fujiko) or someone the target knows to get close to the loot, or to fool security at a venue he's about to hit. It has backfired on him on at least one occasion, when the man he was planning on robbing fell in love and proposed.
 * He also wore a Spy Catsuit resembling that of the resident "beta girl" of Island of Assassins in one scene.
 * Goemon, Jigen, and even Fujiko have also been in cross-gender disguises for jobs, usually most unwillingly. And one volume of the Lupin III Y manga had them all in drag to fool both Zenigata and their target.
 * Zenigata himself has also gotten into the action, in one episode disguising himself as Fujiko, and in Farewell to Nostradamus as a Brazilian carnival girl.
 * In The Woman Called Fujiko Mine episode 6,.

Comicbooks
"Tim: 'I could have been a genius, a Doogie Howser prodigy!'
 * German detective Nick Knatterton did this more than once.
 * The Mighty Thor has a story that adapts the Thrymskvitha poem. This means that, yes, Thor has to dress in a pink wedding gown and pose as Thyrm's bride-to-be while Loki bends over backward explaining why "Freya" is 7 feet tall and just as broad across the shoulders. At least he didn't have to explain away a beard in this version.
 * At least two versions of Robin have done this:
 * In one Batman story, Tim Drake had to disguise himself as a girl to obtain samples from a hospital. Alfred explains that Tim was too young to pull off a male medical student. Tim was not happy about it:

Alfred: 'That would attract too much attention'

Tim: 'These boobs attract too much attention! Did you have to make them so big?'

Alfred: 'They're big enough to give you positive attention, but not enough to be remembered.'

Tim: 'Okay, you put waaaay too much thought into this...'"


 * Tim's not the only Robin to be in drag. Dick Grayson was disguised as Marie Antoinette, Lulu Belle and Batgirl.
 * Rudi and his buddy Freddy do this to visit a New Year's Eve party organized by a group of Straw Feminists. It doesn't end well.
 * Jimmy Olsen does it so often he keeps an extensive wardrobe of womens' clothing and accessories in his "disguise trunk." Strictly because it's necessary for his job as an investigative reporter. Or at least that's what he says. Crazy Prepared reporter or Wholesome Crossdresser who found a way to write off his female wardrobe as a business expense? You make the call!
 * Captain America (comics) and Paladin engage in one of the least convincing examples ever recorded when they have to pass unnoticed through Superia's base filled with female supervillains. They simply take the costumes (which, incidentally, are skintight) of two defeated villains and put them on, with no further attempt at disguise, trusting that the presence of a number of Brawn Hilda types among Superia's followers will be enough to deflect suspicion. It works!.

Fanfiction

 * In the backstory for SpeakingThroughWrittenWords's Hearth universe, Vash saved himself and his younger sister from an arranged marriage by disguising himself as a woman and wiggling out of it, and disguising his sister as a boy so she wouldn't be seen as an option. As of All's Fine That Ends Okay, has caught on to the truth. He takes on the disguise one last time to  and Hilarity Ensues.

Film

 * In Sherlock Holmes: Game of Shadows, Holmes makes use of the paper-thin disguise variation. Mainly for laughs.
 * Mrs. Doubtfire.
 * Classic Example: Some Like It Hot.
 * In The Boondock Saints, the character played by (not exactly feminine in any sense of the word) Willem Dafoe sneaks into a mobster household by putting on a wig and a dress. Despite the disguise being horribly unconvincing, the first man he meets nearly jumps on him.
 * Subverted in that he appears too prepared for the role, too eager to engage in it, and too good at slipping into the character. He's never explicitly stated to be a Cross Dresser, but he's certainly not the wholesome type, as evidenced by a discretionary cut when the flirtation with the mooks seem to be going to another level.
 * In She Zow, Guy wears a female superhero costume to fight crime and save the day http://vimeo.com/38396064
 * The Dustin Hoffman comedy Tootsie, of course. "Dorothy Michaels" becomes quite the man magnet, in fact. His/her own pursuit of a female costar is kind of complicated.
 * Used quite often in The Three Stooges. Especially blatant in these cases because most of the Stooges not only have very obviously male faces, but are... well, exceptionally ugly, even as men. Also, Curly, the largest Stooge, is the one who most frequently has to do this. In fact, in one episode, Curly dresses up as a female Native American to fool a French hunter, who actually goes so far as to marry this "fat Indian momma" and take him/her to his bedroom. Hilarity ensued, although the disguise was revealed before anything truly unfortunate could happen.
 * In Anything for Love (a.k.a. Just One Of The Girls) Chris constantly is pushed around by bully Kurt and his gang. When he has to change to the same school as them, he decides to disguise in women's clothes on his way to school to avoid his tormentors. However already the first morning he runs into two teachers when still dressed up as female - so he's bound to the role. He learns of the advantages soon, when he manages to become best (girl-)friend to cheerleader Marie.
 * The Wayans Brothers' film White Chicks, where they're not only disguising their sex, but their race as well. One even ends up with a Scary Black Man as an admirer.
 * Lots of Carry On films. Usually with cleavage so low and chest hair so thick it verges on Nightmare Fuel.
 * In The Birdcage, this trope is used two different times by several characters. The first instance happens when Nathan Lane's character dressed up as the housewife of his gay lover, played by Robin Williams, in order to impress their future daughter-in-law's ultraconservative parents. In the ending, Everyone except Robin Williams's character and son (and the senator's wife and daughter, who engage in Recursive Crossdressing) dress up in drag in order to escape from the paparazzi.
 * The Birdcage is an Americanized remake of the French theatrical (and later film) comedy La Cage aux Folles, which features the same trope.
 * The film Sorority Boys, where three frat boys Drag it up and join a rival sorority. In a mild subversion to Attractive Bent Gender, one of the boys' admirers is the sorority's bisexual president.
 * Nuns on the Run combines this with Bad Habits.
 * In Willow, Madmartigan disguises himself as a woman in an attempt to hide from a woman's jealous husband. It backfires when said husband finds him attractive and proceeds to proposition him. Right infront of his wife.
 * In Tango and Cash, Cash (played by Kurt Russell), dresses in drag in order to exit a nightclub without the cops becoming suspicious. Cue Russell's male fans screaming in horror.
 * In Total Recall, Douglas Quad tries to infiltrate Mars undetected by disguising himself with an animatronic "fat woman suit".
 * In Brain Donors, handyman Jacques dresses up as a ballerina during the big premiere.
 * In Hes My Girl T. K. Carter dresses in drag so he can accompany his best friend on a trip to Los Angeles. Really.
 * In Armed and Dangerous, John Candy's character and his best friend disguise themselves- John Candy's character dressess like Divine and his best friend (played by Eugene Levy) dressess like the cop from the Village People.
 * John Candy is also seen dressed as a woman at the end of Whos Harry Crumb.
 * Big Mommas House
 * In Don Juan Demarco, the title character is enslaved and purchased by a Sultana, to serve as her, *ahem*, personal attendant. To conceal him from the Sultan, he's disguised as a harem girl; a masquerade he pulls off quite convincingly (being played by Johnny Depp can only help.)
 * In Love Exposure, the protagonist Yu loses a bet and must cross dress in public, kiss a pretty girl, and tell her he loves her. This is also what sets off the bulk of the film's plot.
 * Pee Wee's Big Adventure: Pee-Wee quickly pulls together a drag masquerade while approaching a police roadblock, playing wife to escaped convict Mickey. It's not much of a disguise - just Pee-Wee in a chenille housecoat - but it fools the police and gets a squicky leering gaze from Mickey. Toward movie's end, Pee-Wee also dresses as a nun to sneak onto a movie set and reclaim his bike.
 * Partially in The Master of Disguise.
 * The Little Rascals: Alfalfa and Spanky in ballerina drags. Bullies Butch and Woim find them quite attractive.
 * I Was a Male War Bride is a Very Loosely Based on a True Story 1949 movie wherein French army captain Henri Rochard (Cary Grant) must disguise himself as a nurse in order to accompany his US Women's Army Corps wife back to America after World War II.
 * In One, Two, Three,
 * In Experiment in Terror a bank teller under surveillance by the FBI goes to the ladies room and thinks she's safe even when a hunched over older woman enters. Then she hears the wheezing breath of the man who has been tormenting her.
 * D'Artagnan in The Three Musketeers is forced to escape Milady by dressing in her maid's clothes. Judging from Athos' manservant's reaction to him, he wasn't half-bad as a woman.

Literature
"Hobbie: "Boss, tell me you're not putting us in women's clothing." Wedge: "Very well. I'm not putting us in women's clothing.""
 * In Terry Pratchett's Discworld novel Jingo, after Fred and Nobby's Dressing as the Enemy scheme falls flat, they steal some costumes from a trio of traveling performers: "Gulli, Gulli, and Betti". Nobby gets stuck playing "Betti", an exotic dancer, and his quite homely appearance is explicitly cited in a footnote as being in a heated battle with the Attractive Bent Gender trope.
 * Nobby actually enjoys his experience, to the point where when he goes on patrol to entrap unlicensed thieves targeting ladies of negotiable affection, he insists on playing the bait--even though he's partnered with Angua, who is not only strikingly beautiful but is tough enough to act as her own backup.
 * In Monstrous Regiment,  So of course, as soon as they need to infiltrate a keep,   he is the only one able to pass as a woman.
 * Used very dramatically in the third Finnegan Zwake novel when.
 * In one of the Geronimo Stilton books, Geronimo's Arch Rival uses an Identical Stranger to gain ownership of his newspaper. Geronimo realizes he can uses the same trick to get the newspaper back, and then he and his sister notice their cousin Trap is nearly identical to his Arch Rival except for two things: they have different color fur, and oh yeah, Trap is male and the Arch Rival, Sally, is female. After a day at the salon, Trap becomes the spitting image of Sally, and after a night of watching footage, he's able to mimic her voice flawlessly.
 * In the novel God Stalk, the protagonist (Jaime Kinslayer) was saved/adopted by a soft-hearted innkeeper named Tubain; while living at the inn, she occasionally heard Tubain being berated for his generous impulses behind closed doors by the his wife, Abernia, who never left her rooms. Not until the story is nearly over does Jaime learn Abernia's secret:.
 * At one point in The Adventures of Huckleberry Finn, Huck dresses up as a girl to investigate what's been going on in town since he ran away. After an old woman tests him and eventually sees through it, he has to come up with a new excuse about why he's a boy dressed as a girl.
 * In The Wind in the Willows, Toad escapes from prison disguised as a washerwoman. Later on he blows his own cover when a barge-woman insults his washing abilities and his pride can't take it.
 * In Last Call by Tim Powers, the protagonist dresses in drag to infiltrate a party being hosted by the villain. In defiance of the usual subtropes, nobody is in any doubt about his sex, let alone strangely attracted to him -- but it serves perfectly as a disguise in as much as nobody suspects for a moment that it's him.
 * In the French novel Malevil, there is Bèbelle. A Creepy Crossdresser who uses this trope to his advantage, he pretends to be a woman to infiltrate settlements, prior to his brigand army invading.
 * In Catherine Jinks Evil Genius Trilogy, Cadel cross dresses on multiple occasions and uses this trope to fool his teachers in the academy as a female identity he calls Ariel.
 * There are a couple of examples from the Doctor Who Eighth Doctor Adventures. In The Book of the Still, Fitz is in a sort of Lotus Eater Machine On Drugs, whose creators are trying to come up with an interesting adventure scenario for him. He ends up marrying an evil, lecherous version of the Doctor, disguised in a Pimped Out Wedding Dress as Evil!Doctor's unwilling bride, then having a swordfight, rescuing his Girl of the Week, and flying around with a jetpack, still in the dress. In The Gallifrey Chronicles, it seems that we will wear sequined latex space suits, colourful lipstick, false eyelashes, wigs, and moon boots in the future, at least on Mars. Even if we're men, except for the Doctor. Fitz, who's grabbed the Designated Monkey ball, is in drag again and highly embarrassed, as you would be too, if you were a scrawny (but, as an earlier scene implies, not that toned), thirtysomething guy with a long, stubbly face, in that outfit.
 * Sherlock Holmes at one point disguises as a woman for the purpose of tailing a suspect. He's also (temporarily) fooled by a man in drag in A Study in Scarlet.
 * Played for Laughs in the X Wing Series novel Starfighters of Adumar. Wedge's plan for escaping pursuit in an urban environment involves a camcorder, a truck, "and four sets of Adumari womens' clothing".


 * In The World According to Garp, Garp dresses as a woman to attend his mother's funeral.

Live Action TV

 * The TV series Bosom Buddies was an early 1980s sitcom where two men (Tom Hanks and Peter Scolari) disguised themselves as women to get a New York apartment.
 * This trope does not, as a general rule, apply to Jamie Farr's character, Max Klinger, on Mash. Klinger merely crossdresses to make people think he's crazy, so that he can get a Section 8 psychiatric discharge. However, there are isolated exceptions over the show's long run:
 * Klinger does disguise himself as a woman "for real" in the later-season episodes "Private Finance" and "Taking the Fifth", as well as in an episode of After MASH. He also disguised himself as a Korean woman (with a straw hat pulled down over his face) during the episode "Dear Peggy" so he could sneak out of camp. This failed when Colonel Potter recognized him: "Korean women are not noted for hairy knuckles."
 * In one episode, the only way the 4077th crew can help a South Korean deserter is by disguising him a woman. Who do they go to for advice? Klinger. He looks the man up and down for a second, then says "Size 9, junior miss," and instantly picks the perfect dress for him to wear from his own clothing rack.
 * Murdock does this in the fourth season of The A-Team; in order to get past an angry mob that has the rest of the team holed up, he dresses as a pregnant woman and convinces them that "One of the men in there is the father of my baby!"
 * In Kamen Rider W, the Liar Dopant is lured to an auditorium by Wakana claiming she wants to meet him. Ryu and Akiko dress as Wakana's (male) bodyguards
 * iCarly: In "iWant My Website Back", Spencer disguises himself as a "busty old woman" and an old man gets the hots for him. Even after Spencer blew up his cover that he is really a man, the old geezer still pursued him to his apartment, willing to "start all over again" as long as Spencer wears back the wig.
 * ...Well, nobody's perfect
 * The short-lived 1960s sitcom The Ugliest Girl In Town involved a guy masquerading as a female fashion model in London.
 * The murder victim and/or murderer on Mystery of the Week and Police Procedural shows sometimes turns out to be a cross-dresser.
 * The season 4 episode of Boy Meets World, "Chick Like Me", starts out this way. Cory Mathews is convinced to write something more meaningful for the school paper than his usual bad jokes column. After the class begin discussion of "Black Like Me", an account of a white man's experiences disguised as a black man for a week, he decides to disguise himself as a girl so he could discover how different their experience of high school life was from that of a boy. Having failed to become very feminine, Shawn tries to demonstrate how to do it. They end up finding out that Shawn is a Wholesome Crossdresser in the closet but for the purposes of this episode he is Disguised in Drag, even going out on a date with a boy who doesn't know that he's a boy too, for the purposes of research. Since the episode revolved around sexual harassment, it doubled as a Very Special Episode, ending with Shawn getting a date with a girl he liked because she knew that he now knew what it was like to be the "chick" on a date.
 * They did this again in a later episode, appropriately titled "What A Drag!", in which Jack and Eric dress up as women to avoid the vengeance of a badass who they tried to have arrested. Once again, they turn to Shawn for advice and he provides spot on tips for crossdressing. By the end, Eric decides to give it a try on a more regular basis, just to "Keep in touch with my feminine side."
 * In one episode of A Different World, Dwayne Wayne and Ron Johnson have to dress as women to hide from cocaine dealers who are pursuing them.
 * In the episode "Major Star" of Blackadder Goes Forth, Lieutenant George develops a drag act as part of an attempt to boost troop morale, and 'Georgina' promptly attracts the amorous attentions of General Melchett, which 'she' only escapes by faking 'her' death. A revived drag act featuring the General's driver, Corporal Parkhurst, is dismissed by Melchett as completely unconvincing - even though Corporal Parkhurst is really a woman.
 * In the My Two Dads third-season episode "Kind of a Drag", Michael posed as Joey's wife to get rid of a pesky woman and accidentally became the object of desire for one of Nicole's male teachers.
 * In the season three Halloween Episode of News Radio, Dave dresses as a woman for the annual party. He comments on how depressing it is to learn at 30 that he looks better as a woman than as a man.
 * Dave Foley was well experienced at dressing in drag, due to his time on The Kids in The Hall. (However, neither that show nor Monty Python's Flying Circus really deals in this trope, as the male actors in those sketch comedies were generally playing actual female characters, as opposed to male characters impersonating women.)
 * Used (somehow) completely straight in Star Trek Deep Space Nine, where Quark has to dress up as undergo surgery to become a woman in order to impress someone who can restore an ally of his to power. Every aspect of this trope is invoked, so much so that even his brother finds him attractive, not to mention the actual subject of the ruse. This is partially justified because obviously Ferengi have different standards of beauty than humans and it's possible that Quark might be an attractive one after all. On the other hand, the episode is awful anyway and most fans prefer not to think about it.
 * And yes, the "crossdressing" does require surgery, but this is Star Trek, where apparently any disguise is done with extensive surgery. On the other hand, since this is Star Trek, "extensive surgery" equates to waving a coloured bulb over the patient's stomach.
 * Used in one episode of 3rd Rock from the Sun where Dick dresses as a woman to infiltrate a woman's discussion group his love interest Dr. Albright was attending. Needless to say, Hilarity Ensues.
 * Farscape. Played for drama and laughs in "Coup by Clam", where John Crichton and Rigel dress as women in order to infiltrate a brothel. Crichton gets hit on by a government thug who, in an interesting subversion, already knows that he's a man dressed as a woman as he'd seen Crichton earlier.
 * The Monkees did it twice. In the episode "The Chaperone," Davy's love interest can't attend a party without a chaperone, so Micky dresses as a woman who's chaperoning the party. The girl's father ends up being attracted to him. In "Some Like it Lukewarm," Davy dresses as a girl so that they can enter a band contest for mixed-gender groups. Naturally, the guy running the contest falls for Davy.
 * A very old Sesame Street sketch had Bert do this to fill the role of a princess in the production of a story called "The Magic Apple". And the groom was Ernie. Bert is extremely reluctant to play this part in the sketch.
 * Revisited in the Muppet Family Christmas special, when the Sesame gang performs an enactment of Twas the Night Before Christmas and Bert is dragooned into playing "Mamma in her kerchief" while Ernie is "I in my cap".
 * The Due South episode "Some Like It Red" (a Shout-Out to Some Like It Hot, referring to the "red" of Fraser's Mountie dress uniform) has Fraser going undercover as a teacher in a Catholic girls' school. In drag, he bears an uncanny resemblance to Lucy Lawless, so obviously he fits Attractive Bent Gender as well. The most interesting point is that the actor, Paul Gross, managed to portray a lot of feminine mannerisms in addition to wearing the disguise itself. Straight and gay fans of both genders have confessed to confused feelings for "Ms Fraser".
 * The Jeeves and Wooster episode "The Delayed Arrival" has both Jeeves and Bertie briefly in drag; Jeeves disguised as an American author, and Bertie as a maid.
 * Eric van Helsing. He doesn't even bother to shave first, for chripes' sake.
 * The Third Doctor dresses as a washerwoman in the Doctor Who serial The Green Death. It was just convincing enough to fool an unobservant guard who wasn't looking at him and to pass a message on to Captain Yates ... who promptly began to rib him about it.
 * A tip for escaping from prison in My Name Is Earl: if you're going to disguise yourself as a nurse, make sure you don't look too attractive.
 * In one episode, the boys of The Mighty Boosh disguise themselves as old women to infiltrate a bingo hall in search of a demon granny they'd accidentally summoned. Hilarity ensues, especially seeing as Howard doesn't even shave his mustache
 * An episode of Hercules: The Legendary Journeys has Autolycus and Salmoneus do this as a Whole-Plot Reference to Some Like It Hot. Bonus points for featuring Michael Hurst as The Widow Twanky.
 * This happened a couple of times in Saved by the Bell.
 * Screech had to infiltrate the girls' locker room as an old Irish cleaning woman to record their singing.
 * Zack decided to dress in drag and watch his friends react to his tape announcing that he's going to military school. Nobody was fooled by the disguise.
 * Johnny Depp's attraction to eyeliner didn't start with Captain Jack Sparrow. Way back during 21 Jump Street, he was undercover in drag in "In the Custody of a Clown" and looked far too convincing.
 * In Merlin, Gwen disguises Sir Leon as a female courtier to escape Camelot. While it's mildly Played for Laughs, we never really get to see the finished disguise.
 * LazyTown: Robbie disguises himself as "The Birthday Fairy" and "Miss Roberta".
 * You can also see a variety of ladies' dresses in Robbie's disguise chambers that he has yet to wear.
 * Top Gear's Middle East Christmas Special had the presenters take a meandering journey from Iraq to Bethelehem. Driving through Syria, the guys unexpectedly discovered that Top Gear is extremely popular in Syria. Which posed a problem, because Israel doesn't allow entry to people who have been in Syria. After first attempting to pass through the empty Syrian desert, they then decided to don burqas instead to pass unnoticed. This cunning plan didn't work all that well, as three people in burqas driving bizarrely modified convertible sports coupes still tend to draw attention.
 * On Barney Miller, Sgt. Dietrich signs up to go undercover in drag. He's even good-humored about it, but doesn't realize that he isn't fooling anyone and just ends up embarrassing himself.
 * Actually each member of the squad had his turn doing this duty, with most of the jokes centered on how unattractive the detectives were - except Harris, who, after reluctantly shaving off his mustache, dolled himself up in characteristic style, and was fairly attractive.
 * In one episode of The Sweeney a character played by Warren Mitchell (better known for Till Death Us Do Part) escapes from villains by dressing up in his girlfriend's clothes and a wig. Regan and Carter turn up. "Ooh Mr Wardle, you do look nice!"
 * Big Time Rush has multiple examples:
 * Logan does this thrice. Oh, and one time he's hit on, and the third time the situation is used to help James write a love song.
 * James does this himself in the prom episode.
 * In Victorious, when Tori is terrified of doing a stunt, she makes Beck do it for her by dressing in her same outfit, which he does, oblivious to the rest of her friends.
 * Saturday Night Live mines a lot of comedy from this vein.
 * In a recent digital short, Keenan Thompson (a rotund black man) plays Reba McEntire (not a rotund black man). For the first verse or so, the gag is a fairly simple crossdressing bit. Around the start of the second verse, however, Thompson reveals that, in the skit, he actually is a man dressed as a woman (he does this by bluntly saying "And a penis!" when Andy Samberg sings about all of "Reba's" great attributes). Thompson spends the rest of the song explaining that he found a red wig in a dumpster and Samberg confused him with Reba. He says all of this with Andy standing right next to him. Andy doesn't seem to hear.
 * In the Young Blades episode "The Invincible Sword," Siroc dresses as a woman so he can disguise a bomb, made out of a watermelon, as a pregnant belly. It Makes Sense in Context, mostly.
 * In The Legend of Dick and Dom, the heroes need a potion ingredient from a vampire... Alan, The Vampire Baby. Prince Dom is dressed up as a nanny with giant feeding bottle to try and get close to him.
 * The short-lived 2011 sitcom Work It has two male ex-autoworkers disguising themselves as women in order to land jobs as sales reps for a pharmaceutical company. Incidentally, its cancellation after 2 episodes may have had something to do with the transgender rights groups protesting the show.
 * Astoria, Waldorf's wife, from Episode 13 in Season 4 of The Muppet Show looks like Statler in drag... Which can bring up some Ho Yay... Though there isn't really any proof that it is actually Statler.

Myth and Legend

 * In Norse Mythology, Thor disguises himself as the fertility goddess Freya in order to retrieve his hammer after the king of the giants steals it, and demands her hand in marriage in exchange for its return. Being part of an oral tradition, Hilarity Ensues quite often in the retellings as Loki, playing the part of "Freya's" chaperone, has to maintain his cover by coming up with increasingly convoluted explanations for why the dainty, feminine goddess can eat an entire cow, drink an entire barrel of mead, has a beard, and so forth.
 * In Greek Mythology, Achilles is disguised as a woman due to a prophecy that stated he would die if he went to war. Versions of the myth differ from place to place, but the basic story is he's shipped off to live with the daughters of Lycomedes, king of Skyros, under the name Pyrrha (the red-haired girl). When Odysseus comes looking for him after learning that Troy would not fall without him, he goes to Skyros under the guise of a peddler. He tricks Achilles by laying out perfumes and such, which the daughters all go crazy for, and weapons, which Achilles goes for, instantly blowing his cover.
 * Prince Yamatotakeru, a semi-legendary figure in Japanese Mythology, was said to have dressed as a maidservant to kill members of a rival clan.

Theater

 * Brandon Thomas' 1892 farce Charley's Aunt (later adapted to film several times, and musicalized in 1948 as Where's Charley?) is a classic example.
 * In A Funny Thing Happened on the Way to the Forum, Hysterium is talked into impersonating the "dead" courtesan Philia.
 * Princess Ida, and the narrative poem by Tennyson it was based on, has the protagonists donning women's clothing to infiltrate a women's college.
 * In Richard Strauss' opera Der Rosenkavalier, the 16-year-old boy Octavian is made to dress as a chambermaid for a Honey Trap scheme against Baron Ochs.
 * The page Cherubino is disguised as the Countess's maid to avoid the Count's vengeance in The Marriage of Figaro.

Video Games

 * In Final Fantasy VII, Cloud dresses up as a woman to infiltrate a harem. Depending on your choices in finding components for his disguise, he may be deemed more attractive than the two actual female party members with him.
 * It's also worth noting that, even without the best and sexiest components for his disguise, he's still deemed attractive enough for all of the Don's lackeys to want to bang him.
 * Tales of Vesperia features a chance to do this. When the need arises to seduce your way past a guard, Yuri is given the choice of two of his female party members (Estelle or Judith) or forcing young boy Karol into a pretty pink dress and bow. Worth noting is that using "feminine wiles" on the guard was Karol's idea in the first place, making this perhaps a Karmic punishment.
 * Making things even better, all three of the outfits become purchasable costumes later on in the game, meaning that you can have Karol be wearing his dress whenever you feel like it.
 * In one questline in the Storm Peaks of World of Warcraft, your character gets disguised as a vrykul warrior maiden. This is more than just a disguise, however; if your character is male and has earned the title "Patron", the title automatically changes to "Matron" in every zone where the disguise is in effect.
 * Luigi has done this in the Mario RPGs twice. In Mario & Luigi: Superstar Saga, Luigi was dressed as Peach to get near Fawful and retrieve the Beanstar. He also has done this offscreen in Paper Mario: The Thousand-Year Door, where he had to dress as a beautiful maiden (though most of everyone else around him needed Brain Bleach).
 * Prior to this, a comic published in Nintendo Power had him switch clothes with Peach after the Koopalings caught Mario and threatened to kill him unless the just-escaped princess was returned. (Peach proceeded to wear his overalls for the rest of that arc as she led the others in Storming the Castle.)
 * Romancing SaGa: After his friend Farah is kidnapped, Jamil does this so that he can get into  secret harem. Notably, he dons the dress before trudging through the sewers to North Estamir.
 * Alexander will dress up in Beauty's clothes if you chose the short path in King's Quest VI Heir Today Gone Tomorrow.
 * In Monkey Island 2: LeChuck's Revenge, Guybrush has to wear a lady's dress as a costume in order to sneak into Elaine's Booty Island mansion.
 * Captain Qwark, the so-called "superhero" has a tendency to sneak into places by being disguised... in drag. This is most notable in Up Your Arsenal, and A Crack in Time where he snuck around Nefarious' Space Station as "Nurse Shannon." While his broad shoulders, huge chin, and overall masculine appearance make his disguises very paper thin, he's managed to fool a select few people. (Namely a taxi driver and Clank of all people.)

Web Comics

 * In Order of the Stick, Roy gets turned into a woman by a girdle of masculinity/femininity, and must fend off the amorous advances of his unknowing party-member Belkar (who, of course, knows that it's really Roy and is doing it on purpose just to creep him out).

Web Original

 * The Saga of Tuck opens with Tuck dressing as a girl for Halloween; the irony of this only becomes apparent later.
 * Lee Phillips dresses as a woman in the Kate Modern episode "The Hen Night", in order to attend the hen night (and investigate the ladies' toilets).
 * In The Gungan Council, C'orringath Ven'Traas and Ayin Kaes looked great as handmaidens for the queen of Naboo.

Western Animation
""Where we're going, you won't need any pants!""
 * In every Looney Tunes short where Bugs Bunny dresses as a female to deceive Elmer Fudd, Elmer becomes instantly besotted.
 * Played particularly weirdly in Rabbit of Seville: The climactic battle between Elmer and Bugs degenerates into them alternating chasing each other with more and more deadly weapons...until Bugs abruptly comes up with a series of COURTING GIFTS (flowers, chocolates, and so forth, finishing with a diamond ring) and Elmer runs off and comes back in a WEDDING DRESS.
 * Used in the Chip 'n Dale Rescue Rangers episode "Adventures in Squirrelsitting". Chip 'n Dale not only dressed as a girls, but put on a show in order sneak into Fat Cat's hideout.
 * A stock disguise and diversion in the Tale Spin universe, to the point it might overlap with Wholesome Crossdresser:
 * In the episode "Feminine Air", Baloo dresses as a woman because he wants to take part in a flying competition, but the last sponsor taking any applicants only accepts women. He also gets paired with his female boss as a navigator and has to fool her throughout the episode.
 * In "A Spy In the Ointment", Baloo has to dress up as part of a gypsy performance troupe (And only complains about having to wear uncomfortable boots as opposed to anything else)
 * At one point during "For Whom the Bell Klangs", Louie dresses up as a belly dancer as a distraction.
 * Taking a cue from Looney Tunes, Adventures of Sonic the Hedgehog has this happen a lot with Sonic. Sonic even uses his disguises to seduce Robotnik once in a while. The other characters get into it, too - Scratch does it twice (both times, to seduce Sonic) and Grounder has ended up in bridal garb twice (to Scratch's groom), and dressed as a little girl once.
 * In The Flintstones episode "In the Dough", Fred and Barney disguise themselves as women to enter a baking contest when Wilma and Betty get the measles.
 * The basis of an episode of SpongeBob SquarePants, where Patrick thinks someone is threatening him, so he crossdresses so he can stay, even though he really doesn't need to. Hilarity Ensues when literally every male character besides Spongebob (who's in on the whole thing) to positively go ga-ga over him. From Mr. Krabbs to Squidward, and even Larry the Lobster.
 * Bender does this on Futurama. In the episode "Raging Bender" he is forced to wrestle as the Gender Bender, in a tutu and blonde wig. And in "Bend Her", he undergoes a robo-sex change to compete in the Olympics under the name Coilette.
 * The Family Guy episode "Go, Stewie, Go!" has Stewie disguising himself as a girl on several occasions:
 * To land a role on the American version of his favorite children's show, Jolly Farm. References to both Mrs. Doubtfire and Tootsie also appear in this episode.
 * When the family forced to live in Texas after Quahog citizens believed he's possessed by Satan.
 * South Park examples:
 * Mercilessly parodied in "Butter's Bottom Bitch". The police chief dresses as a female whore as part of a sting operation. At least half a dozen guys fall for this, but the police chief takes the operation a step further and actually HAS SEX with the men looking to solicit prostitution. The police chief takes it ANOTHER step further and actually gets married. To his pimp.
 * Played more or less straight in "Majorine". The boys discover the girls with a cooty-catcher and believe it to be a future-telling device. In order to steal it, they force Butters to fake his own suicide, dress up as a girl and infiltrate the girls' slumber party.
 * Sokka dons the uniform of a Kyoshi Warrior in an early episode of Avatar: The Last Airbender. Suki manages to talk Sokka into feeling pretty good about it...until Aang strolls by and compliments him on his "nice dress".
 * Made even funnier when you consider Aang's comment earlier in the episode:

"Helloooo, everybody! I'm Avatar Kyoshi!"
 * Little did Aang know that he'd be stuck putting on the "nice dress" of the founder of the Kyoshi Warriors only a few scant months later. And then vamping in it.

""And then we met Suki, who's a Kyoshi warrior. She made me dress like a woman, and then she kissed me--" (This was the point where his father stepped in to shut him up, though it took him a few (hilarious) seconds to reach the podium.)"
 * Sokka, at least, never quite lives it down.
 * From a speech explaining his history with the Avatar in front of the entire Black Sun invasion army:


 * In an episode of Rugrats, Tommy's Dad and grandfather dressed him up in a dress and a wig to enter him into a baby beauty contest to win a fishing boat. Tommy's mom was not happy.
 * Hefty Smurf of The Smurfs had to disguise himself as Smurfette to protect her from the unwanted affections of a troll king.
 * No fewer than three episodes of The Perils of Penelope Pitstop had the Hooded Claw do this. In "Cross Country Double Cross", he dressed as an old woman to hitch a ride on Penelope's motorcycle, and in two other episodes he impersonated Penelope herself.
 * In The Problem Solverz episode "K-999 and Da Little Explorerz", Alfe dresses as a girl scout so he can get Nina's missing semaphore badge for her. He changes his name to Alfena, dons glittery makeup, and somehow manages to fool everyone, even though the scouts have a radar that can detect boys in their organization.
 * The titular character of Eek the Cat did this once in the second episode "Bearz 'n the Hood", when he and the Squishy Bears steal laundry clothes from a very grouchy woman and dress as hula girls so they can catch a ride on a pickup truck.
 * Pinky and The Brain are always wearing disguises, and about a third of those involve women's clothes.
 * Yao, Ling, and Chien-Po (and Mulan herself, in a bit of Recursive Crossdressing) at the end of Mulan.
 * Shaggy and Scooby are forced to dress as women in the first episode of Scooby Doo Mystery Incorporated so the team can searched a suspicious location that was hiring female workers.
 * In an early Popeye cartoon, Bluto, to show up Popeye at his ladies-only gym, disguises himself as a woman - an ugly, ugly woman.
 * On The Powerpuff Girls, a trio of hulking convicts come up with the idea of dressing up like the trio to go on a crime spree unhindered (and it works!) They look through their prison cell wondering how they can pull it off - the camera pans from bunks chained to the wall, a toilet, a locker with three Powerpuff Girl costumes...
 * In the Adventures in Care-A-Lot episode "Battle of the Band," Grizzle dons a Wig, Dress, Accent to pose as "Busybody Bear" and spread a little gossip to break up a recently formed band, whose practicing was keeping him from getting any sleep.

Real Life

 * During the 1973 Operation Spring of Youth, in which Israeli special forces attacked key members of terror organisations residing in Lebanon, unit-commander (and future PM of Israel) Ehud Barak was disguised as a brunette woman.
 * In the time of Julius Caesar, Roman politician Claudius disguised himself as a woman in order to infiltrate the Women's Mysteries. He got away with it, until forced to speak. The punishment would have been severe if he hadn't somehow weaseled his way out of it. Afterward he was very angry at the high priestess, a Vestal Virgin and years afterward took revenge on her. (Vestal Virgins could and did abandon their positions. Said priestess got married... but Claudius arranged for her to have a very unsuitable match.)
 * In the first season of Australian Idol, Shane Jenek didn't make it past the auditions (among other things, his voice is unusually high for a guy). He came back the next day dressed as a woman and made the cut as 'Courtney Act'. He was spotted by only one of the judges, but the judges decided he was good enough to keep in. 'Courtney' made 'Final 3', then made the cut at the 'Wild Card' part, and made the finals. In fact, 'she' was one of only three people from that season who got a record deal, and 'she' made it to number 29 in the ARIA charts with the song "Rub Me Wrong". Based on that, FHM magazine picked 'her' as one of the top 100 sexiest women that year. Shane Jenek is still a guy.
 * In Afghanistan, smugglers will often wear burqas to hide what they're smuggling.