"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."
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
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.
If the action is taking place in the Middle East, this may manifest as Hiding in a Hijab
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- 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
- 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).
- 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-.
- In the second season of Vandread, it turns out that BC was a guy the whole time, serving a spy for Tarak.
- 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.
- 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.
- 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.
- Also happens to Tieria in 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.
- 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.
- It's a Running Gag in Ranma ˝ 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 (had he done it as a woman, the Orochi would've made a beeline for her.)
- 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.
- 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.) 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.)
- 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 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...
- 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: 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.
- 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 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?
- 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.
- Axis Powers Hetalia:
- In the YuYu 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 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.
- Conan once switched clothes with Ayumi to find some kidnappers (they wanted her to deliver the ransom.)
- Played with much later: Kaitou knockes out and strips a girl named Sara to disguise himself as her, leaving her only in her undies... but Sara 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 a top without a bra at that moment.) Conan later explains everything, Kaitou is all "WTF?!" when told Sara's a girl... and cue to a very pissed off Sara in her undies drop-kicking him on the head.
- 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 dresses up as a maid in an attempt to rescue Sheryl.
- 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.
- Interestingly, Oz was initially going to be a girl who disguised herself as a man.
- Lupin III 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.
- Samurai Champloo: Jin does this to get into a brothel.
- In JoJo's Bizarre Adventure Part II, 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?
- 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.
- In Candy Candy, Candy spends at least half of the School Festival dressed up as a dashing, playful and very girlish-looking boy.
- 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 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.
- 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 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.
- 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.
- 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 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.
- 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 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:
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...'*
- 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.
- 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 infront 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 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, 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.
- Thunderball opens with Colonel Bouvar, an adversary of Bond's, faking his death and dressing as his widow.
- Pretty much the inspiration for Austin Powers spotting a club employee as one of Dr. Evil's mooks in drag.
- 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".
- 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.
Live Action TV
- 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.
- 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.
- 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.
- 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 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.
- 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 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.
- 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 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.
- 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.
- After the Battle of Culloden in 1746, Bonnie Prince Charlie escaped Scotland by disguising himself as a washerwoman.