"Sirrah, go you to Barthol'mew my page,Any scenario where a man dresses as a woman for purposes of disguise. In many cases, this results in Incredibly Conspicuous Drag, the man 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 Crossdresser. 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 depending on just what fashion he or she likes it. 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, as is Hiding in a Hijab.
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."
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
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- One of the WCW Hotline commercials, which promised callers the dirty secrets of company employees, involved Bobby Heenan and "Mean" Gene Okerlund disguising themselves as waitresses to spy on Sting.
- 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.
"Woman" #2: seeing a man making goo-goo eyes at "Woman" #1) Isn't that Ed from accounting?
Anime and Manga
- In anohana: The Flower We Saw That Day, Yukiatsu disguises himself as Menma to fool the other Peace Busters and to relieve his own obsession of her.
- Axis Powers Hetalia:
- France once dressed up as a girl to capture Italy. The plan is pulled off without a hitch.
"Germany, Germany! I was hitting on someone because I thought it was a cute girl, but it was actually France in disguise!"
- Italy himself once dressed up like a woman on April Fools Day in order to trick Japan.
- France once dressed up as a girl to capture Italy. The plan is pulled off without a hitch.
- Black Butler:
- A plot point for episode 4. And one guess who got dragged into the drag. Give up? Ciel.
- In season two we have Alois briefly disguising himself as a maid.
- Black Cat:
- Train 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.
- In Brave10, because he would have been killed if it were found out any of the original Ishikawa Goemon's sons were living, the Ishikawa Goemon seen in this series starts living as a woman to deter rumours.
- Code Geass had three male characters do this in one of the picture tracks. We had Rivalz and Suzaku◊, but also 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.
- 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.
- Conan Edogawa from Detective Conan and Kaitou Kid from Magic Kaito 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 Kaitou steals Sonoko's mother Tomiko's very expensive black pearl while perfectly disguised as Ran, which strongly implies that he drugged, stripped her and perfectly studied her... er, features so he could pose as her better. Conan himself goes completely red when confronting and unmasking Kaitou, realising the implications of a nude Ran hidden somewhere... Fortunately, Kaitou is polite enough to not steal her gown, only using a similar dress.
- Played with much later: Kaitou knocks out and strips Sera to disguise himself as her, leaving her Bound and Gagged in her undies... but Sera is such a Bifauxnen and so flatchested that he doesn't notice it's a girl. (To be fair she is wearing boyish underwear and an undershirt at that moment. Sera was also caught in the men's washroom because the women's washroom was full.) Conan later explains everything, Kaitou is all "WTF?!" when told Sera's a girl... and cue to a very pissed off Sera in her undies drop-kicking him in the head.
- Conan once switched clothes with Ayumi to find some kidnappers (they wanted her to deliver the ransom.)
- In Dual! Parallel Trouble Adventure, the local Humongous Mecha can only be piloted by females. So when the male protagonist shows he's compatible, the Mad Scientist in charge of the robots makes up a female-looking pilot suit with voice changer and "shock absorbers". It doesn't last very long.
- In El-Hazard: The Magnificent World, 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.
- The Evillious Chronicles have two examples which make for shocking twists in The Daughter of Evil and The Lunacy Of Duke Venomania; in the former, Allen Avadonia dresses up as his twin sister to take her place on the chopping block, and in the latter Kachess Crim dresses as the sorceress Elluka to infiltrate the lustful Duke Venomania's harem and stab him without being suspected.
- In Fist of the North Star, Rei, one of the characters in the series, does this to lure his pursuers into a trap by using his pink cloak and hide his face, but mainly for survival. Then makes his epic reveal when his real gender is shown. It works because of his Bishōnen looks, and he's been trying to find a man with seven scars on his chest (who was revealed to be Jagi, Kenshiro's evil brother who was framing and impersonating him).
- There's one scene in episode 7 of Fractale where Clain Necran does this while roaming a city populated by Doppels.
- Fullmetal Alchemist
- Edward Elric has disguised himself as a girl only once in the first anime. Whether or not that was successful would be difficult to say.
- Lt. General Grumman disguises himself as an old woman at one point to meet with Mustang.
- 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.
- In the Get Backers 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...
- A major plot element in the first half of Turn A Gundam, where the protagonist Loran is put into situations where he is forced to crossdress 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.
- Happens to Tieria in Mobile Suit Gundam 00, when he must infiltrate a high-class party. The thing is, he's androgynous enough to 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.
- Mobile Suit Gundam ZZ had the male members of the Gundam Team crossdressing in order to infiltrate a enemy base (It Makes Sense in Context). Humorously, while Iino gets in easily, Judau gets turned away because he looks downright weird in a dress.
- Hare from Haré+Guu was disguised as a girl once.
- 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...)
- Although not normally used as a disguise, Hermione Ayasaki is once used as such in an alternate story of Hayate the Combat Butler, 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 the manga version of Honoo No Alpen Rose, Jeudi crossdresses and cuts her hair to escape from the Count, and a local girl named Liesl hits on "him" (and may be a bit enamoured with "her" even after finding out, and at some point in the manga, Leonhart does this as well.
- 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. At the end of the series, very subtle hints are dropped that his landlady is actually a man in drag, who does so in order to be close to the headmistress.
- In JoJo's Bizarre Adventure: Battle Tendency, Joseph Joestar decides that the best way to infiltrate a secret Nazi base in Mexico is to don a Harmless Lady Disguise. Since Joseph is over six feet tall and incredibly muscular, you can imagine how well it worked out.
Joseph: Damn, those Nazis are impressive. How could they see through my female disguise?
- One-shot Kanojo Ni Naritai!? is about a high school boy who pretends to be a girl to date a classmate who he thinks is a Butch Lesbian. It turns out she is unattracted to girls though.
- In the manga adaptation for Kingdom Hearts: 358/2 Days, Roxas was forced to wear a French Maid Outfit and pretend to be the White Rabbit's servant, Mary Ann, while trespassing his home to find a way to restore Luxord to his normal size. Unfortunately, it didn't work.
- Kyo Kara Maoh!:
- This is how Yuuri first meets Jozak, whose disguise would have been more convincing if Jozak didn't a) have noticeably larger biceps than most women and b) seem to believe that Sleeves Are for Wimps.
- Jozak is the only one that does it regularly, but if the characters in general need to go somewhere in disguise, there's about a fifty-fifty chance that at least some of them will be going there in women's clothes. It's that kind of a series.
- Lupin III:
- Lupin is a Master of Disguise and does this often. Either disguising himself as a female ally (such as Femme Fatale Fujiko), 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. The reveal did not dissuade him.
- He also wore a Spy Catsuit resembling that of the resident "beta girl" of Lupin III: Island of Assassins in one scene.
- Goemon, Jigen, and Fujiko (the latter as Lupin himself in at least one case) 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 Lupin III: The Woman Called Fujiko Mine episode 6: Oscar disguises himself as the targeted schoolgirl to trick Fujiko and Lupin.
- Unsurprisingly pulled off by Alto Saotome in Macross Frontier Sayonara no Tsubasa where he dresses up as a maid in an attempt to rescue Sheryl.
- 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-.
- Mint Na Bokura is about a boy who disguises himself as a girl so that he can attend the same boarding school as his sister.
- In Monster Rancher, Hare devises a plan to sneak Holly and the Stone safely away from their enemies, by having Genki and Holly swap outfits and then have Genki run interference while Holly slips quietly away with Tiger. Unfortunately, Lillim was Dangerously Genre Savvy enough to see through it.
- 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.
- Pandora Hearts:
- In 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.
- Interestingly, Oz was initially going to be a girl who disguised herself as a man.
- In the first season of the 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, though usually it's not a disguise.
- In Unova Ash, Pikachu, and Cilan had to crossdress in order to get into an all-girls club.
- The aforementioned Running Gag reversed itself in Kalos in one episode when it's Serena who has to masquerade as Ash while he's incapacitated.
- 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.) Logically, then, this also applies to Jessie, who has dressed as a man on several occasions (though she doesn't seem to crossdress as much as James does.) They've mostly stopped crossdressing since Johto but it will sometimes pop up.
- Ranma ˝:
- It's a Running Gag 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 (namely, a schoolgirl, a nurse, a policewoman, and a bride.) The funniest part is that Ranma does this as a man (had he done it as a woman, the Orochi would've made a beeline for her.)
- In Rinne, 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.
Rinne: How do I look?
Tsubasa: How am I supposed to answer that?
- 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.
- Samurai Champloo: Jin does this to get into a brothel. However despite his Bishōnen looks, the thugs guarding the brothel are suspicious and insist he play the instrument he's carrying. Jin fails dismally and so whips off his disguise.
Thug: Crossdressers! I mean...double-crossers!
- In Shounen Oujo (literally Boy Princess), Albert is a peasant child in a matriarchal society who is bought by the princess Alexia (whom he greatly resembles), in order to serve as her decoy while she sneaks out to see the queendom she will one day rule. The twelve-year old Alexia is assassinated at her coming-of-age ceremony and Albert steps in to take her place on the spur of the moment, leading to him spending the next two years posing as a girl in every aspect of his lifestyle, going so far as to use herbal and beauty treatments to stave off puberty.
- 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 Bizarro Episode instead.
- In Tokyo Ghoul:re, Haise Sasaki goes undercover on a mission to learn about the ghoul auction with his group of investigators (the Qs), and everybody except for Saiko (already female) dress up as women because the ghoul they were investigating, Nutcracker, was recently targeting young women to lure them into the auction.
- In the second season of Vandread, it turns out that BC was a guy the whole time, serving a spy for Tarak.
- 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.
- Aoi from You're Under Arrest! had to dress as a woman in order to catch chikan. Eventually she began living full-time.
- 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 YuYu Hakusho manga, Yusuke pulled this off pretty well and look like quite a convincing girl believe it or not.
- 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:
Tim: 'I could have been a genius, a Doogie Howser prodigy!'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...'*
- In one Batman story, Tim Drake had to disguise himself as a female medical student to obtain samples from a hospital. Alfred explains that Tim was too young to pull off a male med student. Tim was not happy about it:
- 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 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!.*
- Fanhunter: The Liquidator, a parody of Terminator, is a muscled male robot coming from the future. Naked, he looks for the clothes of a nearby person. He uses the clothes of a female Flamenco dancer, believing it is some kind of urban camouflage gear. It's a comedy after all.
- "Cuckoo in the Nest" from Tammy. It was a unique entry in girl's comics, as the main character was a boy who had to pose as a girl (his name was Leslie, but his aunt thought he was a girl named "Lesley", and the money his uncle used to spoil him was to be used pay on school fees at a girl's school, so when the uncle learned that the aunt was going to visit Leslie at the end of term, he had to enroll Leslie at the school and make him pose as a girl for the entire school year or go to prison).
- At one point in Super Mario Adventures, Luigi disguises himself as Princess Peach in order to distract the Koopalings, leaving Peach dressed in Luigi's clothes.
- Back in the 40s retired actor Richard Stanton fought crime under the alias Madam Fatal.
- 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'', only Roderich Edelstein, who Vash was supposed to marry, has caught on to the truth. He takes on the disguise one last time to get Mrs. Edelstein to leave Roderich alone and Hilarity Ensues.
- The AU Fullmetal Alchemist Edvy fanfiction The Seven Names of Envy Angevin involves this as a fairly significant part of the plot, having Envy disguise himself as 'Julia Vasquez', a flirty, sexy Hispanic girl immigrating from the States. It's also how he figures out he likes guys.
- Played with in the Hivefled prequel Reprise: Gamzee escapes from the Grand Highblood's torture chamber and manages to pass unnoticed through the ship while wearing clothes he stole from a female recruit. The male and female subjugglator uniforms don't look different enough for this to really be an example externally, but since a small but painful part of the mental torture inflicted on him involved mockery of his effeminate qualities, it's really not helping his trauma.
- Done twice in Calvin and Hobbes III: Double Trouble — Calvin is forced to do this by Chill early on, and later Retro dresses as an old lady in order to hitch a ride.
Films — Animated
- In the beginning of Disney's Robin Hood Robin and Little John disguise themselves as gypsy women in order to rob Prince John. Robin pulls it off quite convincingly, his buddy, would have been revealed if he spoke to anyone up close.
- Kung Fu Panda 2. Po while trying to sneak past the wolf guards. Doubles as Paper-Thin Disguise, since it consists of only a kite, two watermelons, and a fan. When a leering wolf moves in for a closer inspection, Po headbutts him in the face.
- At the end of Mulan, Yao, Ling, and Chien-Po (and Mulan herself, in a bit of Recursive Crossdressing) do this to sneak past the Huns. Made even funnier by the reprise of "I'll Make a Man Out of You" playing in the background.
Films — Live-Action
- Bob Hope does this in The Princess and the Pirate in order to avoid being chucked overboard by said pirate.
- In Sherlock Holmes: A Game of Shadows, Holmes makes use of the paper-thin disguise variation. Mainly for laughs.
- Mrs. Doubtfire.
- Classic Example and the one providing the picture above: 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 Crossdresser, 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.
- The Dustin Hoffman comedy Tootsie. "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 terrifying.
- 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. Thanks 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 in front of his wife.
- In Tango & Cash, Cash (played by Kurt Russell), dresses in drag in order to exit a nightclub without the cops becoming suspicious. Cue Russell's male and female fans screaming in horror...
- In the original Total Recall (1990), Douglas Quaid 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 Momma's 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 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, Right-hand man Schlemmer disguises in Sexy Secretary Ingeborg's dress to fool the Russians, so they'll let Otto free.
- 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.
- Diamonds Are Forever has Blofeld leaving his casino/hotel base disguised as an old lady.
- In Like Flint - Flint's boss Kramden tries infiltrating a woman-run organization in a very unconvincing drag disguise.
- Revenge of the Pink Panther - Clouseau picks up someone he thinks is a woman, but is a criminal known for his female disguise. He forces Clouseau to exchange clothes and takes his car...Clouseau is subsequently picked up by his fellow police, and he unnecessarily explains "Do not let my legs fool you, I am really a man!"
- Freddy Krueger does this in A Nightmare on Elm Street 4: The Dream Master. When Kristen falls asleep in the school nurse's office, Freddy disguises himself as the nurse to mess with her, before reverting back to his nightmare form.
- Cannonball Run II has Victor (Dom De Luise) J.J. (Burt Reynolds) and Morris (Sammy Davis, Jr..) dressed up as exotic dancers to get in to the ranch the race's kidnapped sponsor has been taken to. note
- The two male protagonists do this in the film Ski Party, and it's even noted by one of them that they're "play[ing] Some Like It Hot".
- Girl Happy: Yes, folks, Elvis in drag.
- The 1975 Soviet film Hello, I'm Your Aunt! (loosely based on Brandon Thomas's play Charley's Aunt) has a homeless man being blackmailed by two young gentlemen named Charlie and Jackie into pretending to be Charlie's aunt who is due to arrive from Brazil. The "aunt" (a wealthy widow) is supposed to seduce a judge and convince him to let his two nieces marry Charlie and Jackie before they're 25. Then the real aunt arrives. Hilarity Ensues.
- In On the Double Danny Kaye tries to hide from a couple of Nazi officers by disguising himself as a female nightclub singer.
- One of the segments in Woody Allen's Everything You Always Wanted to Know About Sex* (*But Were Afraid to Ask) involves a secret transvestite who, through a series of complications, gets caught outside while dressed in a woman's clothes and attempts to pass himself off as female (while covering his large mustache with his hand) while a large crowd gathers.
- In Paddington, Mr Brown disguises himself as a female cleaner to infiltrate the Geographer's Guild.
- Mr Headmistress involves a thief (played by Harland Williams), who just got out of prison and is being chased by a bunch of thugs who want him to pay off a very large debt. While escaping on a train, he accidentally runs into a middle-aged woman and takes her luggage. He escapes from the thugs by dressing as her, which causes him to be mistaken for a new headmistress about to take charge of an all-girl boarding school. Not only does he have to keep his Number Two, the teachers, and the students unaware of his identity, but he has to find a way to pay off the bad guys, so they stop looking for him. Naturally, Hilarity Ensues. At the end, after the ruse is discovered and the bad guys are arrested, he is invited to stay on as the first headmaster.
- In The North Avenue Irregulars, Rose doesn't drive so her husband Delaney agrees to drive for her, reluctantly dressing in drag so The Mafia doesn't recognize him.
- In the 1975 film The White, The Yellow, The Black, all three main characters do this to rescue a village's women. Their cover is blown when the thugs tear off Black Jack's small veil covering his mustache, and a fight ensues.
- In The Hobbit: The Battle of the Five Armies, Alfrid hides among the women and children disguised as a woman to avoid joining the battle. The women decide to pick up weapons and join their husbands, and he still refuses to help, making him look even more pathetic.
- In A Brother's Price a male character disguises as female prostitute. However, as men are rare in the setting, female prostitutes try to look like men, to appeal to their female customers, most of whom consider themselves heterosexual. Which means that he is a man, who disguises as a woman, who disguises as man. Due to the gender roles in that setting, the appearance he is ultimately described as having is somewhat Drag Queen like.
- Terry Pratchett's Discworld:
- In 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. The trope loses. No mean feat in a world that runs on tropes the way RoundWorld runs on physics. 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, The Squad is forced to dress up as men to join the army. So, as soon as they need to infiltrate a keep, the Lieutenant, utterly oblivious to the fact that he is the only actual man in the group, declares that he is the only one able to pass as a woman. He's actually right.
- Escaping from prison disguised as a washerwoman is briefly mentioned in three books: In The Last Continent, Rincewind is going through all the standard escape tropes with a Genre Savvy guard, and is disappointed to learn the washerwoman is said guard's mum. In The Last Hero, Contractually Genre Blind Evil Harry Dread has a jailer who's described as letting a bearded washerwoman in Incredibly Conspicuous Drag out of the cell without a second thought. And in Raising Steam, reformed conman Moist recalls visiting Quirm in a variety of different disguises, and once as a different sex. A footnote adds that the jailers didn't figure out how he escaped until they realised the laundry never came back.
- Used very dramatically in the third Finnegan Zwake novel when Sheridan Shakespeare disguises himself as Nada Kloo.
- 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: She's Tubain in drag, yelling at himself.
- 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 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 and to escape Thaddeus Roth as a female identity he calls Ariel.
- In the Doctor Who Eighth Doctor Adventures novel 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.
- Sherlock Holmes at one point disguises himself as an old lady for the purpose of tailing a suspect, who kindly picks up his parasol for him. 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".
Hobbie: "Boss, tell me you're not putting us in women's clothing."
- In The World According to Garp, Garp dresses as a woman to attend his mother's funeral.
- In Gary Jennings' The Journeyer, Marco Polo's clothes accidentally get burnt in a fire. The girl who does it offers him some of her clothes. He puts them on to avoid getting the girl in trouble.
- In the Rainbow Magic series, the goblins do this all the time, especially in the Fashion Fairies series. One Princess Fairy book has a goblin dressed as a princess, with the narration calling him Princess Goblina.
- How Hope uses Cradock to get Magawisca out of jail in Hope Leslie.
- In the children's book Miss Nelson Has a Field Day, the principal, Mr. Blandsworth, tries the "Miss Viola Swamp" schtick on the school football team and fails spectacularly ("Oh rats! How can they tell?"), leading Miss Nelson to take matters into her own hands.
Live Action TV
- In The Adventures of Superman episode "Double Trouble", one of the crooks disguises himself as a woman to get through customs.
- 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 M*A*S*H. Klinger merely crossdresses in an attempt 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 AfterMASH. 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 "Till Death Do Us Part", Murdock poses as the bride at a wedding while the rest of the team help the real bride escape.
- In Kamen Rider Double, 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 and Philip dresses up as Wakana herself. Akiko is bewildered by how convincing a woman he makes, having been completely fooled until the reveal, and the gender confusion causes her to faint.
- 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.
- The short-lived 1960s sitcom The Ugliest Girl In Town involved a guy masquerading as a female fashion model in London.
- Occurred at least twice on Boy Meets World:
- In "Chick Like Me", 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.
- In "What A Drag!", 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 NewsRadio, Davenote dresses as a woman for the annual Halloween party. He comments on how depressing it is to learn at 30 that he looks better as a woman than as a man.
- Even funnier is when Lisa complains that he's wearing HER dress - and it looks better on HIM.
- Used (somehow) completely straight in Star Trek: Deep Space Nine, where Quark has to
dress up asundergo 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, plus 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.
- 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.
- Jack did this a couple of times on Three's Company. In one, he thinks the authorities are after him and dresses up as a woman (he claims to be Chrissy) to get past them. In a later episode, he entered a recipe contest as "Grandma Tripper" and dressed the part when he's selected as a finalist.
- 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.
- 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 (2008), 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.
- On Barney Miller, each member of the squad ends up going undercover in drag:
- Sgt. Dietrich is good-humored about it, but doesn't realize that he isn't fooling anyone and just ends up embarrassing himself.
- Harris, 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:
- 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 one 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.
- The Muppet Show looks exactly like Statler in drag. There isn't really any suggestion that it is Statler, but for those with Ho Yay theories.... Astoria, Waldorf's wife, from Episode 13 in Season 4 of
- In an episode of Hogan's Heroes, Newkirk attends an officer's wives party like this, as he's impersonating a spy whose regular MO is this.
- Every Allied main but Kinch has cross-dressed at least once—Hogan, Newkirk and LeBeau in "I Look Better in Basic Black", and Carter in "Reverent Kommandant Klink" (that one was for stage purposes, not espionage). Besides the aforementioned officers' wives party, Newkirk gets in drag in at least three or four episodes.
- In the second episode of MythQuest, Thor show Alex!Vali what happened the last time his hammer was stolen: He dressed up as his wife, whom the theif wanted to marry, and sat through a wedding feast before revealing his identity.
- On Sanford and Son Fred learned the new hot tenant at his motel Sanford Arms he has the hots for was a high-end fence. Through obvious means he gets him to confess, but the undercover cop staying at his house dismisses it due to the obvious legal matters. Best friend Bubba manages to successfully bust the crook by cross-dressing, winning the thousand dollar reward Fred and even Lamont were desperate for.
- One episode of The Closer had a suspect disguised as his girlfriend to throw off the cops. He uses it for working on a cruise ship. The disguise is so good that Det. Sanchez was flirting with him and kissing him. Sanchez went to therapy after that.
- The finale of Gilligan's Island sees Mr. Howell, the Skipper, and the Professor trying to pass as women in order to fool the natives into thinking they're goddesses. Gilligan turns out being the only one able to dupe them, and, naturally, Attractive Bent-Gender ensues.
- The guys from Top Gear did this using Syrian style burqas during the Middle East Special because the current political situation meant that having it be known they'd gone from Syria to Israel even after passing through Jordan might cause them to be denied entry. As usual for Top Gear, it was Ambitious but Rubbish, as they found when they arrived in Damascus.
May: [Sees 'Welcome Top Gear' sign on hotel] I've appeared on television, in drag, for nothing!
- One sketch by The Two Ronnies has them as stuffy commuters, who arrive at their station and chat about everyday topics, as they change into flamboyant ladies' outfits. The punchline: They're doing it because the station only has a ladies' lavatory.
- The fourth episode of the series Sun Trap has Woody dressed as a female croupier so that he can investigate the disappearance of a large amount of money from the local casino. It is unnerving how brazenly he flirts with one of the customers, who fortunately doesn't realize.
- Murder, She Wrote: In "The Great Twain Robbery", the murderer sneaks up on what would be his next victim, only to discover it is a male police officer disguised in drag.
- Toward the end of the Vocaloid song "The Madness of Duke Venomania", KAITO disguises himself as a woman in order to rescue his lover from the mad duke's harem. It works, and he reveals himself after stabbing Venomania with a poisoned blade.
- The cover◊ of The Rolling Stones' 1966 single "Have You Seen Your Mother, Baby, Standing in the Shadow?" has five airplane stewardesses who are really the Stones themselves.
- *NSYNC's music video for their song "U Drive Me Crazy" had them disguise themselves as the Spice Girls in an attempt to get the attention of a music executive. It crosses over into Incredibly Conspicuous Drag because Joey Fatone and Chris Kirkpatrick were still sporting facial hair.
- Queen's video for "I Want To Break Free" has the guys all dressed as women, and is a homage to the British TV show Coronation Street.
- The folksong Patrick Street (and several variants) feature a sailor forced by circumstances to wear women's clothing.
Myth And Legend
- Norse Mythology: In the Poetic Edda ("Thrymskvida"), 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 a cow, drink a 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.
- Rikishi disguised himself as a woman when Eric Bischoff went looking for a lesbian to hire and send after Stephanie McMahon.
- Macaela Mercedes's personal referee, Whipme Spearz, became such after Mercedes found he was trying to pass himself off as a woman so he could compete for PGWA and GLORY and became her lackey to prevent being outed.
- Stevie Richards in WWE after Victoria inexplicably stopped being a psycho path and went back to her goofy dancer gimmick. She didn't want anything to do with him suddenly, because Ricards was still crazy, so he started following her around, ruining Victoria's matches when in plain clothes but aiding her while disguised as a woman.
- Trent Barreta as "Girl From Mexico" in his attempt to win the FCW Divas Championship after the company was revived by WWE.
- Santino Marella and Beth Phoenix's relationship became strained when Santino began disguising himself as his "sister" Santina, so "she" could win the miss wrestlemania crown.
- 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. In both this and the Der Rosenkavalier case above, the character is already being played by a woman.
- Shakespeare has a lot of Sweet Polly Oliver characters, but the only time he uses the reverse situation is in The Merry Wives of Windsor, in which Falstaff disguises himself as the extremely fat Witch of Brainford in order to get out of the Fords' house after Master Ford comes home early. Hilarity, naturally, ensues.
- In The Complete History Of America Abridged, three soldiers trapped behind enemy lines in World War I hatch a Zany Scheme to escape: dressing up not as Germans but as The Andrews Sisters, an anachronism justified by the Rule of Funny.
- 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.
- Tales of Graces has this when the party performs a play version of Snow White in Velanik. For some reason, the role of the Evil Queen doesn't go to Pascal or Sophie...but to Hubert. Of course he's completely unwilling and a rather stiff actor. The "disguise" part comes in when a man in the crowd recognizes Hubert as Strahta's top Lieutenant. In order to protect his identity, Hubert goes full-bore Large Ham, complete with squeaky feminine voice, and the spectator concludes that no respectable officer would be caught dead crossdressing on stage.
- 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 Wuhan's secret harem. Notably, he dons the dress before trudging through the sewers to North Estamir.
- Alexander will dress up in Beauty's clothes for re-entry into the castle 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.)
- This is how Michael gains access to the Lady Land of Shecola in StarTropics.
- In a drama CD Yuuya of Hatoful Boyfriend puts on a maid outfit for a stakeout. He's a bird and of a species where males and females look alike - it's specifically noted that dresses are a common element in jobs high school boys take - and it probably would have gone unnoticed if two schoolmates hadn't recognized him.
- The actual gender of Jazzpunk's protagonist Polyblank is not elaborated on in-game, but the live-action teaser trailer features a man. In the third mission, you have to disguise yourself with a wig and lipstick in order to cozy up to an enemy agent and then covertly switch out his briefcase with a dummy. The agent seems quite taken with disguised-you, but it turns out to be an act; he's onto you and has you drugged and dumped in an unoccupied hotel room, sans briefcase.
- One portion of Summon Night Swordscraft Story 2 involves you needing to get past a monster to progress, however he won't let someone without sex appeal go through. A character named Bryon ends up dressing as a woman to try and convince the monster to let him through.
- In Castlevania RPG, Alec has several times disguised. When he disguises to infiltrate the Ranger's Guild castle with Jennifer and Cassandra Belmont, they're captured because the latter doesn't look female enough.
- In Divine Bells, Hong-Ryeong dresses as a maid at one point to avoid detection while sneaking around his palace.
- In Drowtales, Nau'kheol and Khal'harror are forced into this so they can sneak into the girls' section of the school. They're assisted by Sorane'sanil, who does this on a regular basis, and while Sorane gets caught because one of the teachers recognizes him, the other two manage to pass.
- In Far to the North a group of Saengorian slavers cover themselves to avoid attracting the attention of the Goblin who guards the woods near the Rethuii, the native peoples of the North, since their dark hair makes them a target and the Goblin apparently won't attack women regardless of their ethnicity.
- In The 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 fellow party member Belkar (who knows that it's really Roy and is doing it on purpose just to creep him out).
- Dillon, the title character of Sticky Dilly Buns, is a Camp Gay actor with a gift for cross-dressing (as was previously illustrated when he was a secondary character in Ménage ŕ 3; some readers found him quite unnervingly attractive). He uses this for disguise at least once — but then, the Rule of Funny ensures that he meets at least a couple of people who know him well enough to see through the disguise instantly.
- The Saga of Tuck opens with Tuck dressing as a girl for Halloween; the irony of this only becomes apparent later. Tuck soon befriends a large number of his girlfriend's friends, but must keep crossdressing since their parents only trust him because they believe that he's a girl. Then it turns out that a lot of them, his girlfriend included, prefer his female persona. Then he gets a job as a babysitter from a woman who thinks he's a girl. Eventually, he actually finds out that he's a late blooming hermaphrodite, which is the reason he has started being called "miss" even when he's not crossdressing.
- Lee Phillips dresses as a woman in the KateModern 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.
- Louie and Dewey dress up as the Spice Girls in Ducktalez 6, as part of Darkwing's distraction.
- 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.
- 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.
- 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.
- 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".
"Where we're going, you won't need any pants!"
- Made even funnier when you consider Aang's comment earlier in the episode:
- 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.
- 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 to sneak into Fat Cat's hideout.
- 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.
- Timmy in The Fairly OddParents! episode "Operation: Dinkleberg" is dragged into one of his Dad's plots in spying on Mr. Dinkleberg, and has to deliver a box of pastries with a camera in them dressed as a girl scout.
- 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) mainly because as he was waitng to get an audition, he was informed that all the male roles in the show were filled.
- In another episode the family is forced to live in Texas thanks to the population of Quahog believing Stewie is possessed. Stewie ends up competing in a child beauty pagent.
- 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.
- 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.
- In Episode 60 of Kaeloo, Stumpy tries to gain access to a nightclub, but the bouncer refuses to let him in since it's only for girls. He comes back in a wig claiming to be a girl, and is granted access.
- In the Mickey Mouse (2013) short "Shifting Gears", Mickey's living car is uncooperative in letting Mickey take it to the beach, so one of his plans is to get in it disguised as Minnie. When the real Minnie appears, Mickey's disguises quickly falls apart and he instantly grows a 5 o'clock shadow.
- My Little Pony: Friendship Is Magic:
- In "Rarity Investigates!", Wind Rider disguises himself as a mare in an attempt to frame Rainbow Dash for a crime.
- In "Brotherhooves Social", Big Macintosh disguises himself as a mare so that he can compete in the Sisterhooves Social events with his little sister. His disguise fools exactly one person. He ends up getting disqualified, not because of the drag (the judges knew it was him and didn't care), but because of his unsportsmanlike conduct during the race.
- 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.
- Pinky and the Brain are always wearing disguises, and about a third of those involve women's clothes.
- In an early Popeye cartoon, Bluto, to show up Popeye at his ladies-only gym, disguises himself as a woman - an ugly, ugly woman.
- In a WWII cartoon, Popeye and Bluto are both Navy men - Bluto feigns illness to get out of work and asks a sympathetic Popeye for 'a pretty nurse'...Popeye then sees he's perfectly fine and disguises himself as a nurse. Bluto is horrified.
- On The Powerpuff Girls, a trio of hulking convicts come up with the idea of dressing up like the girls 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 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.
- Gus does this in the final episode of Recess as part of T.J.'s plan to get their baseball bat from the Ashleys.
- 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.
- Doowee from Sally Bollywood has had to disguise himself as a girl on a few occasions. In "The Egg War" he ended up dressed up in one of Sally's saris (complete with a wig and makeup) in order to download a message off a girl's phone, and in another episode he ended up dressed as Little Red Riding Hood, in order to get onstage.
- Scooby-Doo examples:
- 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. This is despite both Daphne and Velma being on hand to do so themselves, which Shaggy questions. Daphne gives them a simple answer: She and Velma refused to do it.
- In two of the Scooby-Doo DVD animated movies, Shaggy is dressed as Daphne and Scooby is dressed as Velma.
- The plot of Scooby-Doo in Arabian Nights centers around Shaggy disguising himself as a harem and then having the Caliph wanting to marry him. Shaggy has to pull a Scheherezade Gambit to get out of the wedding.
- The entire premise of SheZow has the male protagonist inheriting his aunt's secret identity, an extremely Smurfette Principle-inspired superheroine. It's convincing enough to fool his own dad, a cop who has a long-standing beef with SheZow.
- Hefty Smurf of The Smurfs had to disguise himself as Smurfette to protect her from the unwanted affections of a troll king.
- 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 "Marjorine". 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.
- In an episode of SpongeBob SquarePants Patrick wrongly thinks someone is threatening him, so he crossdresses so he can stay. Hilarity Ensues when every male character besides Spongebob (who's in on the whole thing) to positively go ga-ga over him. From Mr. Krabs to Squidward, and Larry the Lobster.
- In "The Cent of Money", Mr. Krabs tries to exploit Gary's apparent ability to attract money by going to the arcade dressed as a woman, with Gary hidden under the dress to make him look pregnant.
- A stock disguise and diversion in the TaleSpin 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. Which he doesn't; at the end, he learns that she recgnized him all along.
- 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.
- In the very first episode of What's with Andy?, Andy tries to annoy his sister Jen by mimicking everything she does. This becomes a problem for him when Jen decides to go to the school dance in a dress.
- 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 Gaius Julius Caesar, Roman politician Clodius 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 Clodius 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 man). Since he just so happens to also perform as a Drag Queen and one who can pass as a natural woman, he came back the next day as his drag persona 'Courtney Act' and made the cut. He was spotted by only one of the judges, but they 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.
- For what it's worth, Jenek is one of the few Australian Idol alumni to gain worldwide fame, thanks entirely to his drag persona. He eventually relocated to the United States and, in addition to becoming a successful Youtube personality as Courtney Act, went on to compete in the sixth season of RuPaul's Drag Race and placed in the Top 3.
- In Afghanistan, smugglers will often wear burqas to hide what they're smuggling.
- At the beginning of The American Civil War, May, 1861, when secessionist troops were gathering at Camp Jackson in Missouri, it is said that the Unionist commander of troops in the area, Nathaniel Lyon, decided to scout the camp riding in a carriage disguised as Frank Blair's mother-in-law. Including a black mourning veil. To cover up his beard.
- At the end of the war, there was a rumor in the Union that Confederate President Jefferson Davis was captured wearing women's clothing. This was echoed in numerous newspapers and political cartoons. However, most historians agree that this rumor was false.
- There was a similar rumor about Abraham Lincoln after he was elected having to sneak into Washington DC by train disguised as a woman. While they did indeed have to sneak him in, fearing that he might be assassinated, the crossdressing part was false and probably wouldn't have worked too well since a 6'4" woman would have attracted quite a bit of attention.
- After the Battle of Culloden in 1746, Bonnie Prince Charlie escaped Scotland by disguising himself as a washerwoman.
- According to a urban legend in China, the much esteemed founder of Communist China, Chairman Mao Zedong, should once have done this in his younger days to evade capture by the very anti-Communist regime in China at the time. With the reverence the general Chinese views Mao with, don't expect many to be willing to discuss this rumor, much less confirm it, though.