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[[quoteright:330:[[Film/SomeLikeItHot http://static.tvtropes.org/pmwiki/pub/images/SLIH_330_121.jpg]]]]
[[caption-width-right:330:[[UnsettlingGenderReveal Yep, these are a couple of dudes.]]]]

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

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

Frequently, but not invariably, PlayedForLaughs. May result in AnAesop about [[InAnotherMansShoes 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 WholesomeCrossdresser or CreepyCrossdresser depending on just what fashion he or she ''likes'' it.

SweetPollyOliver is the DistaffCounterpart of this trope, but is more likely to be PlayedForDrama.

HarmlessLadyDisguise is a subtrope.

If the action is taking place in the Middle East, this may manifest as HidingInAHijab.

----
!!Examples:

[[foldercontrol]]

[[folder:Advertising]]
* 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)'' [[{{Squick}} Isn't that Ed from accounting?]]
[[/folder]]

[[folder:Anime and Manga]]
* In ''Manga/FistOfTheNorthStar'', 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 {{Bishonen}} 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).
* ''MazingerZ'': 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 CreepyCrossdresser since it was pretty squicky -and eerie-.
* In the second season of ''Anime/{{Vandread}}'', it turns out that [[spoiler:BC was a guy the whole time]], serving a spy for [[spoiler:Tarak]].
* ''CodeGeass'' had three male characters do this in one of the picture tracks. We had [[http://static.tvtropes.org/pmwiki/pub/images/Yhlothere.jpg Rivalz and Suzaku]], but also [[http://static.tvtropes.org/pmwiki/pub/images/Luluko.jpg Lelouch]]. In a later one, Lelouch was forced into a bridal dress. This scene was then added into the visual novel game [[http://www.youtube.com/watch?v=DKxR2bRas7k 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 [[http://www.youtube.com/watch?v=beLDfKNFs8w&feature=related not quite as attractive, or convincing.]]
* This is the premise of ''IMyMeStrawberryEggs'', wherein the protagonist dresses as a woman to teach at a school run by a misandric headmistress. [[spoiler: 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 ''Anime/TurnAGundam'', 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 [[spoiler:Tieria]] in ''{{Gundam 00}}'', when he must infiltrate a high-class party. The thing is, he's [[DudeLooksLikeALady 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.
* ''GundamZZ'' had the male members of the Gundam Team crossdressing in order to infiltrate a enemy base (ItMakesSenseInContext). Humorously, while Iino gets in easily, Judau gets turned away because he looks downright ''weird'' in a dress.
* It's a RunningGag in ''RanmaOneHalf'' that, whenever Ranma [[GenderBender turns into a girl]] and dons a PaperThinDisguise (which is often little more than a WigDressAccent or a [[ClarkKenting 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 [[TransformationRay Jusenkyo]] turned Ranma into a [[AttractiveBentGender beautiful girl]], whereas he [[InvoluntaryShapeshifting was turned into a small black piglet]].
** In order to distract the {{Orochi}}, a [[AttackOfThe50FootWhatever giant]] pervert who loves girls (to look at as much as to eat,) [[GenderBender Ranma]], Ryouga, [[{{Bishonen}} Shinnosuke]], and [[{{Squick}} Shinnosuke's Grandpa]] crossdress as {{Fetish Fuel Station Attendant}}s (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''.
** [[IdiotHero Gourry]] also has to disguise himself as a woman in a couple other episodes ([[RunningGag always episode 17 of the season]]). Only ''Evolution-R'' averts this tradition, being a BizarroEpisode instead.
* In one episode of ''[[YuGiOh5Ds 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 ''Anime/{{Pokemon}}'' 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 RunningGag OnceASeason.
** If Team Rocket uses a disguise that involves a female and a male role, James will almost always dress as the female. ([[AttractiveBentGender 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 ''DNAngel'', Satoshi disguises himself as a woman in order to distract HandsomeLech Dark during a heist. It works -- he [[HoYay 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 ''FushigiYuugi'' (and a series of short segments after some of the anime {{OAV}}s), 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 GentleGiant 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 [[AttractiveBentGender adorably gorgeous]] young woman, prompting a jealous reaction from Nuriko, who's been [[WholesomeCrossdresser crossdressing]] since the beginning of the series and is horrified that someone might make a prettier woman than him.
* Hare from [[JungleWaItsumoHaleNochiGuu Haré+Guu]] was disguised as a girl once.
* Train from ''Manga/BlackCat'' 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 [[TykeBomb 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 [[http://www.desertmoon.org/screen/blackcat/ep09/bc09_285.jpg Sven]], also in the anime. Y'see, they needed bait to lure out a SerialKiller 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.
* ''[[HarukanaruTokiNoNakaDe 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 [[CastFullOfPrettyBoys 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 [[{{Bishonen}} pretty enough to pass as a girl without much effort]]; the man they were trying to fool even offers "her" to become his wife upon discovering that "she" is not the princess he was searching for, but a different girl...)
* In the ''GetBackers'' manga, this is one of Ban's *ahem* genius plans to try to get them into a prison. He has both him and Ginji dress in school girl uniforms and try to pretend that they're on a field trip and want to visit the prison. It doesn't work. Though they actually ''do'' look [[http://www.mangafox.com/manga/get_backers/v26/c218/42.html quite cute in it...]]
* Although not normally used as a disguise, Hermione Ayasaki is once used as such in an alternate story, to keep [[Manga/HayateTheCombatButler 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 Disguise}}s within the series.
* In ''Anime/ElHazardTheMagnificentWorld'', 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 [[UnsettlingGenderReveal a very uncomfortable moment]] with the princess' lesbian consort.
* In ''OtomeWaBokuNiKoishiteru'', 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 ''Manga/BlackButler''. 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 ''Manga/{{Rinne}}'', [[TheHero Rinne]] decides to dress in a [[{{Meido}} maid uniform]] to try and [[PaperThinDisguise capture]] a [[PunchClockVillain damashigami]] who is kidnapping school girls. It works. He actually has to [[TheUntwist unmask himself]] as male to his opponent when he [[NinjaMaid defeats]] him. He then [[WhatTheHellHero takes advantage of]] his situation to win the school's Mr. Lady competition. While [[TheHeroine Sakura]] and her female friends agree he looks [[MoeMoe cute]], [[TheRival Tsubasa]] is at a loss for words.
-->'''Rinne:''' How do I look?\\
'''Tsubasa:''' How am I supposed to answer that?
* In ''Manga/WildRock'', because Yuuen is an incompetent huntsman and a bit of a runt his father gets him to dress up as a women for a HoneyTrap ploy to get more food.
* ''Webcomic/AxisPowersHetalia'':
** [[MoeAnthropomorphism France]] once dressed up as a girl to capture [[TheDitz Italy]]. [[AttractiveBentGender 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.
* In the ''YuYuHakusho'' manga, [[http://www.mangarush.com/manga/yu-yu-hakusho/171/p-8 Yusuke pulled this off pretty well and look like quite a convincing girl believe it or not.]]
* [[DetectiveConan Conan Edogawa]] [[ArcWelding and]] [[MagicKaito 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 {{squick}}y and funny since [[spoiler: 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, [[ChivalrousPervert Kaitou]] is polite enough to ''not'' steal her gown, only using a similar dress.]]
** [[spoiler: Conan]] once switched clothes with [[spoiler: Ayumi]] to find some kidnappers (they wanted her to deliver the ransom.)
** Played with much later: [[spoiler: 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 [[{{Pettanko}} 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 [[DynamicEntry a very pissed off Sara in her undies drop-kicking him on the head]].]]
* Edward Elric himself from ''Manga/FullmetalAlchemist'' 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 ''RosarioToVampire'', [[TheHero 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 [[DudeLooksLikeALady Alto]] [[AttractiveBentGender Saotome]] in ''MacrossFrontier [[TheMovie Sayonara no Tsubasa]]'' where he [[spoiler: dresses up as a maid in an attempt to rescue Sheryl]].
* In ''PandoraHearts'' retrace 48 Oz briefly disguises himself as a maid with Alice. And [[AttractiveBentGender looked damn good in it]]. Gil even [[HoYay 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 [[WhatCouldHaveBeen initially]] going to be a girl who [[SweetPollyOliver disguised herself as a man]].
* ''Franchise/LupinIII'' is a MasterOfDisguise and does this often. Either disguising himself as a female ally (such as FemmeFatale 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 SpyCatsuit resembling that of the resident "beta girl" of ''Anime/LupinIIIIslandOfAssassins'' in one scene.
** Goemon, Jigen, and Fujiko have also been in cross-gender disguises for jobs, usually most unwillingly. And one volume of the ''Lupin III Y'' manga had them ''all'' in drag to fool both Zenigata and their target.
** Zenigata himself has also gotten into the action, in one episode disguising himself as Fujiko, and in ''Anime/FarewellToNostradamus'' as a [[FanDisservice Brazilian carnival girl]].
** In ''Anime/LupinIIITheWomanCalledFujikoMine'' episode 6: [[spoiler:Oscar disguises himself as the targeted schoolgirl to trick Fujiko and Lupin.]]
* ''SamuraiChamploo'': Jin does this to get into a brothel.
* In ''Manga/JoJosBizarreAdventure'' Part II, Joseph Joestar decides that the best way to infiltrate a secret Nazi base in Mexico is to don a HarmlessLadyDisguise. 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 ''Manga/HonooNoAlpenRose'', [[spoiler:Jeudi crossdresses ''and'' cuts her hair to escape from the Count, and a local girl named Liesl hits on "him" (and may be [[IfItsYouItsOkay a bit enamoured with "her" even after finding out]],]] and at some point in the manga, [[spoiler:Leonhart]] does this as well.
* In CandyCandy, Candy spends at least half of the SchoolFestival dressed up as a dashing, playful and very girlish-looking boy.
* In MonsterRancher, 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 AnoHanaTheFlowerWeSawThatDay, [[spoiler:Yukiatsu disguises himself as Menma to fool the other Peace Busters and to relieve his own obsession of her.]]
* ''Manga/MintNaBokura'' 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 ''Manga/KingdomHearts358DaysOver2'', Roxas was forced to wear a FrenchMaidOutfit 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 ''Anime/DualParallelTroubleAdventure'', the local HumongousMecha can only be piloted by females. So when the male protagonist shows he's compatible, the MadScientist 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 Franchise/EvilliousChronicles have two examples which make for shocking twists in [[LightNovel/ClotureofYellow The Daughter of Evil]] and LightNovel/TheLunacyOfDukeVenomania; in the former, Allen Avadonia dresses up [[spoiler:as his twin sister to take her place on the chopping block,]] and in the latter Kachess Crim [[spoiler:dresses as the sorceress Elluka to infiltrate the lustful Duke Venomania's harem and stab him without being suspected.]]
[[/folder]]

[[folder:Comicbooks]]
* German detective ''ComicStrip/NickKnatterton'' did this more than once.
* ''TheMightyThor'' has a story that adapts the [[NorseMythology 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 Comicbook/{{Robin}} have done this:
** In one ''Franchise/{{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:
--> '''Tim:''' 'I could have been a genius, a [[DoogieHowserMD 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...'[[labelnote:*]]''Batman'' #626 (2004)''[[/labelnote]]
** Tim's not the only Robin to be in drag. Dick Grayson was disguised as [[http://www.the-isb.com/?p=1364 Marie Antoinette]], [[http://discowing.tumblr.com/post/2612174797/this-is-one-of-the-reasons-golden-age-was-both#tumblr_notes Lulu Belle]] and [[http://discowing.tumblr.com/post/3021189741/dick-grayson-a-boy-with-a-crush-a-thespian-a#tumblr_notes Batgirl]].
* ''ComicStrip/{{Rudi}}'' and his buddy Freddy do this to visit a New Year's Eve party organized by a group of {{Straw Feminist}}s. It doesn't end well.
* JimmyOlsen 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''. CrazyPrepared reporter or WholesomeCrossdresser who found a way to write off his female wardrobe as a business expense? You make the call!
* CaptainAmerica 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 BrawnHilda types among Superia's followers will be enough to deflect suspicion. [[CrazyEnoughToWork It works!]].[[labelnote:*]]''CaptainAmerica'' #387-392 (1991)[[/labelnote]]
* ''{{Fanhunter}}'': The Liquidator, a parody of [[TheTerminator 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.
[[/folder]]

[[folder:Fanfiction]]
* In the backstory for [[http://www.fanfiction.net/u/1059080/SpeakingThroughWrittenWords SpeakingThroughWrittenWords's]] [[AxisPowersHetalia 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 [[http://www.fanfiction.net/s/6110201/1/Alls_Fine_That_Ends_Okay ''All's Fine That Ends Okay'']], [[spoiler:only Roderich Edelstein, who Vash was supposed to marry,]] has caught on to the truth. He takes on the disguise one last time to [[spoiler:get Mrs. Edelstein to leave Roderich alone]] and HilarityEnsues.
* The AU ''Manga/FullmetalAlchemist'' Edvy fanfiction [[http://www.fanfiction.net/s/7986051/1/The_Seven_Names_of_Envy_Angevin 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 ''FanFic/{{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 ''Fanfic/CalvinAndHobbesIIIDoubleTrouble'' -- Calvin is forced to do this by Chill early on, and later Retro dresses as an old lady in order to hitch a ride.
[[/folder]]

[[folder:Films -- Animated]]
* ''WesternAnimation/KungFuPanda2''. Po while trying to sneak past the wolf guards. Doubles as PaperThinDisguise, since it consists of only a kite, [[GettingCrapPastTheRadar two watermelons]], and a fan. When a leering wolf moves in for a closer inspection, Po [[UseYourHead headbutts him in the face]].
* At the end of ''Disney/{{Mulan}}'', Yao, Ling, and Chien-Po (and Mulan herself, in a bit of RecursiveCrossdressing) 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.
[[/folder]]

[[folder:Films -- Live-Action]]
* Creator/BobHope does this in ''Film/ThePrincessAndThePirate'' in order to avoid being chucked overboard by said pirate.
* In ''Film/SherlockHolmesAGameOfShadows'', Holmes makes use of the paper-thin disguise variation. [[PlayedForLaughs Mainly for laughs]].
* ''Film/MrsDoubtfire''.
* Classic Example and the one providing the picture above: ''SomeLikeItHot''.
* In ''TheBoondockSaints'', 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 [[WholesomeCrossdresser wholesome type]], as evidenced by a discretionary cut when the flirtation with the mooks seem to be going to another level.
* The DustinHoffman 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 ''Film/TheThreeStooges''. 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. [[HilarityEnsues Hilarity ensued]], although the disguise was revealed before anything truly unfortunate could happen.
* In ''Anything for Love'' (a.k.a. ''JustOneOfTheGirls'') 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 ''WhiteChicks'', where they're not only disguising their sex, but their race as well. One even ends up with a ScaryBlackMan as an admirer.
* Lots of ''Film/CarryOn'' films. Usually with cleavage so low and chest hair so thick it verges on terrifying.
* In ''Film/TheBirdcage'', 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 RecursiveCrossdressing) 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 ''LaCageAuxFolles'', which features the same trope.
* The film ''SororityBoys'', where three frat boys Drag it up and join a rival sorority. Thanks to AttractiveBentGender, one of the boys' admirers is the sorority's bisexual president.
* ''NunsOnTheRun'' combines this with BadHabits.
* In ''Film/{{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 [[AttractiveBentGender attractive]] and proceeds to proposition him. [[DoubleStandard Right infront of his wife]].
* In ''Film/TangoAndCash'', Cash ([[BadAss played by]] Creator/KurtRussell), 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 ''Film/TotalRecall1990'', Douglas Quaid tries to infiltrate Mars undetected by disguising himself with an animatronic "fat woman suit".
* In ''BrainDonors'', handyman Jacques dresses up as a ballerina during the big premiere.
* In ''HesMyGirl'' T. K. Carter dresses in drag so he can accompany his best friend on a trip to Los Angeles. Really.
* In ''ArmedAndDangerous'', 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 VillagePeople.
* John Candy is also seen dressed as a woman at the end of ''WhosHarryCrumb''.
* ''BigMommasHouse''
* In ''DonJuanDemarco'', the title character is enslaved and purchased by a Sultana, to serve as her, *ahem*, [[SexSlave personal attendant]]. To conceal him from the Sultan, he's disguised as a harem girl; a masquerade he pulls off [[http://www.deppimpact.com/gallery/albums/caps_djd/djd389.JPG quite convincingly]] (being played by JohnnyDepp can only help.)
* In ''LoveExposure'', 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.
* ''Film/PeeWeesBigAdventure'': 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 ''TheMasterOfDisguise''.
* ''TheLittleRascals'': Alfalfa and Spanky in ballerina drags. Bullies Butch and Woim [[AttractiveBentGender find them quite attractive]].
* ''IWasAMaleWarBride'' is a VeryLooselyBasedOnATrueStory 1949 movie wherein French army captain Henri Rochard (CaryGrant) must disguise himself as a nurse in order to accompany his US Women's Army Corps wife back to America after UsefulNotes/WorldWarII.
* In ''OneTwoThree'', [[spoiler:Right-hand man Schlemmer disguises in SexySecretary Ingeborg's dress to fool the [[DirtyCommies Russians]], so they'll [[ZanyScheme 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 ''Film/TheThreeMusketeers'' is forced to escape [[TheVamp Milady]] by dressing in her maid's clothes. Judging from Athos' manservant's reaction to him, [[AttractiveBentGender he wasn't half-bad as a woman]].
* ''Film/DiamondsAreForever'' has Blofeld leaving his casino/hotel base disguised as an old lady.
** ''Film/{{Thunderball}}'' opens with Colonel Bouvar, an adversary of Bond's, faking his death and dressing as his widow.
*** Pretty much the inspiration for AustinPowers spotting a club employee as one of Dr. Evil's mooks in drag.
* ''InLikeFlint'' - Flint's boss Kramden tries infiltrating a woman-run organization in a very unconvincing drag disguise.
* ''RevengeOfThePinkPanther'' - 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 ''Film/ANightmareOnElmStreet4TheDreamMaster''. 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.
* ''[[Film/TheCannonballRun Cannonball Run II]]'' has Victor (Creator/DomDeLuise) J.J. (Creator/BurtReynolds) and Morris (Creator/SammyDavisJr.) dressed up as exotic dancers to get in to the ranch the race's kidnapped sponsor has been taken to. [[note]]BrainBleach is recommended.[[/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. HilarityEnsues.
* 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 Creator/WoodyAllen'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 [[SpontaneousCrowdFormation a large crowd gathers]].
[[/folder]]

[[folder:Literature]]
* In Creator/TerryPratchett's ''Literature/{{Discworld}}'' novel ''Discworld/{{Jingo}}'', after Fred and Nobby's DressingAsTheEnemy 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 AttractiveBentGender trope. [[spoiler: 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 [[UnusualEuphemism 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'', [[spoiler: TheSquad is [[SweetPollyOliver forced to dress up as men]] to join the army.]] So, as soon as they need to infiltrate a keep, [[spoiler: 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.
* Used ''very'' dramatically in the third ''FinneganZwake'' novel when [[spoiler:Sheridan Shakespeare disguises himself as Nada Kloo]].
* In one of the ''GeronimoStilton'' books, Geronimo's [[SitcomArchnemesis Arch Rival]] uses an IdenticalStranger 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 ''[[Literature/ChroniclesOfTheKencyrath 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: [[spoiler: She's Tubain in drag, yelling at himself]].
* At one point in ''Literature/TheAdventuresOfHuckleberryFinn'', 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 ''TheWindInTheWillows'', 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 Creator/TimPowers, 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 [[AttractiveBentGender 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 ''{{Literature/Malevil}}'', there is Bèbelle. A CreepyCrossdresser 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 ''EvilGeniusTrilogy'', Cadel cross dresses on multiple occasions and uses this trope to fool his teachers in the academy [[spoiler: and to escape Thaddeus Roth ]]as a female identity he calls Ariel.
* In the ''Series/DoctorWho'' Literature/EighthDoctorAdventures novel ''The Book of the Still'', Fitz is in a sort of LotusEaterMachine [[WhatDoYouMeanItWasntMadeOnDrugs 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 [[PimpedOutDress Pimped Out Wedding Dress]] as Evil!Doctor's unwilling bride, then having a swordfight, rescuing his GirlOfTheWeek, and flying around with a jetpack, still in the dress.
* Literature/SherlockHolmes 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''.
* PlayedForLaughs in the XWingSeries 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."
-->'''Wedge:''' "[[ExactWords Very well]]. [[BlatantLies I'm 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' ''Literature/TheJourneyer'', 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 ''Literature/RainbowMagic'' 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.
[[/folder]]

[[folder:Live Action TV]]
* In ''Series/TheAdventuresOfSuperman'' episode "[[Recap/TheAdventuresOfSupermanS1E15DoubleTrouble Double Trouble]]", one of the crooks disguises himself as a woman to get through customs.
* The TV series ''Series/BosomBuddies'' was an early 1980s sitcom where two men (Creator/TomHanks and Creator/PeterScolari) 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 ''Series/{{MASH}}''. Klinger merely [[WholesomeCrossdresser crossdresses]] to make people think he's crazy, so that he can get a Section 8 psychiatric discharge. However, there are isolated exceptions over the show's long run:
** Klinger does disguise himself as a woman "for real" in the later-season episodes "Private Finance" and "Taking the Fifth", as well as in an episode of ''Series/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 ''Series/TheATeam''; 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 ''Series/KamenRiderDouble'', 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 [[spoiler: 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.
** ...[[SomeLikeItHot Well, nobody's perfect]]
* The short-lived 1960s sitcom ''TheUgliestGirlInTown'' involved a guy masquerading as a female fashion model in London.
* Occurred at least twice on ''BoyMeetsWorld'':
** 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, [[HeterosexualLifePartners Shawn]] tries to demonstrate how to do it. They end up finding out that Shawn is a WholesomeCrossdresser in the closet but for the purposes of this episode he is DisguisedInDrag, 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 VerySpecialEpisode, 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 [[WholesomeCrossdresser "Keep in touch with my feminine side."]]
* In one episode of ''Series/ADifferentWorld'', 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 ''[[Series/BlackAdder 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 [[SweetPollyOliver really a woman]].
* In the ''Series/MyTwoDads'' 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 HalloweenEpisode of ''NewsRadio'', Dave[[note]]played by Dave Foley, who had prior experience as a member of ''Series/TheKidsInTheHall''[[/note]] 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 ''Series/StarTrekDeepSpaceNine'', where Quark has to [[strike:dress up as]] [[WeWillNotUseStageMakeUpInTheFuture undergo surgery to become]] a woman in order to impress someone who can restore an ally of his to power. Every aspect of this trope is invoked, so much so that even his ''brother'' finds him attractive, plus the actual subject of the ruse. This is [[JustifiedTrope 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 [[UnfortunateImplications awful anyway]] and [[FanonDiscontinuity most fans prefer not to think about it]].
** And yes, the "crossdressing" does require surgery, but this is ''Franchise/StarTrek'', where apparently ''any'' disguise is done with extensive surgery. On the other hand, since this ''is'' Franchise/StarTrek, "extensive surgery" equates to waving a coloured bulb over the patient's stomach.
* Used in one episode of ''ThirdRockFromTheSun'' where Dick dresses as a woman to infiltrate a woman's discussion group his love interest Dr. Albright was attending. Needless to say, HilarityEnsues.
* ''Series/{{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, [[FoeYay 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 ''ThreesCompany''. 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.
* ''TheMonkees'' 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 ''Series/DueSouth'' episode "Some Like It Red" (a ShoutOut to ''SomeLikeItHot'', 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 AttractiveBentGender 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 ''Series/JeevesAndWooster'' episode "The Delayed Arrival" has both Jeeves and Bertie briefly in drag; Jeeves disguised as an American author, and Bertie as a maid.
* [[YoungDracula Eric van Helsing.]] He doesn't even bother to shave first, for chripes' sake.
* The Third Doctor dresses as a washerwoman in the ''Series/DoctorWho'' 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 ''MyNameIsEarl'': if you're going to disguise yourself as a nurse, [[BlackComedyRape make sure you don't look too attractive]].
* In one episode, the boys of ''TheMightyBoosh'' 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 [[PaperThinDisguise doesn't even shave his mustache]]
* An episode of ''HerculesTheLegendaryJourneys'' has Autolycus and Salmoneus do this as a WholePlotReference to ''SomeLikeItHot''. Bonus points for featuring Michael Hurst as The Widow Twanky.
* This happened a couple of times in ''SavedByTheBell''.
** 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.
* JohnnyDepp's attraction to eyeliner didn't start with [[PiratesOfTheCaribbean Captain Jack Sparrow]]. ''Way'' back during ''Series/TwentyOneJumpStreet'', he was undercover in drag in "[[http://www.youtube.com/watch?v=B4bJr_gY2E0#t=4m34 In the Custody of a Clown]]" and looked far too convincing.
* In ''Series/{{Merlin}}'', Gwen disguises Sir Leon as a female courtier to escape Camelot. While it's mildly PlayedForLaughs, we never really get to see the finished disguise.
* ''Series/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 [[CreepyCrossdresser has yet to wear]].
* On ''BarneyMiller'', 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 ''Series/TheSweeney'' a character played by Warren Mitchell (better known for ''Series/TillDeathUsDoPart'') 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!"
* ''Series/BigTimeRush'' has multiple examples:
** [[TheSmartGuy Logan]] does this ''thrice''. Oh, and [[AttractiveBentGender one time he's hit on]], and the third time the situation is used to help James write a love song.
** James does this himself in the prom episode.
* In ''{{Victorious}}'', when Tori is terrified of doing a stunt, she makes Beck do it for her by dressing in her same outfit, which he does, oblivious to the rest of her friends.
* ''SaturdayNightLive'' mines a lot of comedy from this vein. In one digital short, Keenan Thompson (a rotund black man) plays RebaMcEntire (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 ''Series/YoungBlades'' episode "The Invincible Sword," [[GadgeteerGenius Siroc]] dresses as a woman so he can disguise a bomb, made out of a watermelon, as a pregnant belly. ItMakesSenseInContext, mostly.
* In ''Series/TheLegendOfDickAndDom'', the heroes need a potion ingredient from a vampire... [[OminousMundanity 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 ''Series/WorkIt'' 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.
* [[invoked]]Astoria, Waldorf's wife, from Episode 13 in Season 4 of ''TheMuppetShow'' looks exactly like Statler in drag. There isn't really any suggestion that it ''is'' Statler, but for those with HoYay theories....
* In an episode of ''Series/HogansHeroes'', 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 ''Series/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 SanfordAndSon Fred learned the new hot tenant at his motel [[SpinOffBabies Sanford Arms]] he has the hots for was a high-end fence. Through [[WhatAnIdiot 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 ''Series/TheCloser'' 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 Series/GilligansIsland sees Mr. Howell, the Skipper, and the Professor trying to pass as women in order to fool the natives into [[ItMakesSenseInContext thinking they're goddesses]]. Gilligan turns out being the only one able to dupe them, and, naturally, AttractiveBentGender ensues.
* The guys from ''Series/TopGear'' 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. [[FailureIsTheOnlyOption 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!
[[/folder]]

[[folder:Music]]
* Toward the end of the {{Vocaloid}} song [[http://www.youtube.com/watch?v=hx8tru8TbaA "The Madness of Duke Venomania"]], [[spoiler: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 [[spoiler:stabbing Venomania with a poisoned blade.]]
* The [[http://images.45cat.com/the-rolling-stones-have-you-seen-your-mother-baby-standing-in-the-shadow-1966-5.jpg cover]] of TheRollingStones' 1966 single "Have You Seen Your Mother, Baby, Standing in the Shadow?" has five airplane stewardesses who are really the Stones themselves.
* Music/{{NSYNC}}'s music video for their song "U Drive Me Crazy" had them disguise themselves as the Music/SpiceGirls in an attempt to get the attention of a music executive. It crosses over into IncrediblyConspicuousDrag 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.
[[/folder]]

[[folder:Myth And Legend]]
* NorseMythology: In the ''Literature/PoeticEdda'' ("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, HilarityEnsues 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 GreekMythology, 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 JapaneseMythology, was said to have dressed as a maidservant to kill members of a rival clan.
[[/folder]]

[[folder:Professional Wrestling]]
* Wrestling/StevieRichards in WWE after [[Wrestling/LisaMarieVaron 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.[[/folder]]

[[folder:Theater]]
* Brandon Thomas' 1892 farce ''Charley's Aunt'' (later adapted to film several times, and musicalized in 1948 as ''Where's Charley?'') is a classic example.
* In ''AFunnyThingHappenedOnTheWayToTheForum'', Hysterium is talked into impersonating the "dead" courtesan Philia.
* ''PrincessIda'', 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 ''Theatre/DerRosenkavalier'', the 16-year-old boy Octavian is made to dress as a chambermaid for a HoneyTrap scheme against Baron Ochs.
* The page Cherubino is disguised as the Countess's maid to avoid the Count's vengeance in ''Theatre/TheMarriageOfFigaro''. In both this and the ''Der Rosenkavalier'' case above, the character is [[RecursiveCrossdressing already being played by a woman]].
* [[JustForFun/TheZerothLawOfTropeExamples Shakespeare]] has a lot of SweetPollyOliver 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. [[HilarityEnsues Hilarity, naturally, ensues.]]
[[/folder]]

[[folder:Video Games]]
* In ''VideoGame/FinalFantasyVII'', 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 [[EvenTheGuysWantHim want to bang him]].
* ''VideoGame/TalesOfVesperia'' 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.
** ''VideoGame/TalesOfGraces'' 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 ''[[CrowningMomentOfFunny 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 [[spoiler: Strahta's top Lieutenant.]] In order to protect his identity, Hubert goes full-bore LargeHam, complete with squeaky feminine voice, and the spectator concludes that no respectable [[spoiler: officer]] would be caught dead crossdressing on stage.
* In one questline in the Storm Peaks of ''WorldOfWarcraft,'' 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.
* [[SuperMarioBros Luigi]] has done this in the Mario [=RPGs=] twice. In ''[[VideoGame/MarioAndLuigiSuperstarSaga Mario & Luigi: Superstar Saga]]'', Luigi was dressed as Peach to get near Fawful and retrieve the Beanstar. He also has done this offscreen in ''VideoGame/PaperMarioTheThousandYearDoor'', where he had to dress as a beautiful maiden (though most of everyone else around him needed BrainBleach).
** Prior to this, a comic published in ''Magazine/NintendoPower'' 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 StormingTheCastle.)
* ''RomancingSaGa'': After his [[LoveInterest friend]] [[{{Tsundere}} Farah]] is kidnapped, [[LoveableRogue Jamil]] does this so that he can get into [[spoiler: 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 [[spoiler:for re-entry into the castle]] if you chose the short path in ''VideoGame/KingsQuestVIHeirTodayGoneTomorrow''.
* In ''VideoGame/MonkeyIsland2LeChucksRevenge'', Guybrush has to wear a lady's dress as a costume in order to sneak into Elaine's Booty Island mansion.
* [[RatchetandClank Captain Qwark]], the so-called "superhero" has a tendency to sneak into places by being disguised... in drag. This is most notable in [[RatchetAndClankUpYourArsenal Up Your Arsenal]], and [[RatchetAndClankFutureACrackInTime 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'' [[PaperThinDisguise paper thin]], he's managed to fool a select few people. (Namely a taxi driver and ''[[InsufferableGenius Clank]]'' of ''all'' people.)
* This is how Michael gains access to the LadyLand of Shecola in ''Videogame/StarTropics''.
* In a drama CD Yuuya of ''VisualNovel/HatofulBoyfriend'' puts on a maid outfit for a stakeout. He's [[UpliftedAnimal 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.
[[/folder]]

[[folder:Web Comics]]
* In ''Webcomic/CastlevaniaRPG'', 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 ''Webcomic/DivineBells'', Hong-Ryeong dresses as a maid at one point to avoid detection while sneaking around his palace.
* In ''Webcomic/{{Drowtales}}'', Nau'kheol and Khal'harror are [[http://www.drowtales.com/mainarchive.php?sid=7067 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 [[http://www.drowtales.com/mainarchive.php?sid=7071 Sorane gets caught]] because one of the teachers recognizes him, the other two manage to pass.
* In ''Webcomic/TheOrderOfTheStick'', 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 ''Webcomic/StickyDillyBuns'', is a CampGay actor with a gift for cross-dressing (as was previously illustrated when he was a secondary character in ''Webcomic/MenageA3''; some readers found him quite unnervingly {{attractive|BentGender}}). He uses this for disguise at least once -- but then, the RuleOfFunny ensures that he meets at least a couple of people who know him well enough to see through the disguise instantly.
[[/folder]]

[[folder:Web Original]]
* ''[[http://www.barkingduck.net/ehayes/index.html The Saga of Tuck]]'' opens with Tuck dressing as a girl for Halloween; [[{{Transsexual}} the irony of this]] only becomes apparent later. [[spoiler: 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 [[WondrousLadiesRoom ladies' toilets]]).
* In ''TheGunganCouncil'', 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 ''WebAnimation/{{Ducktalez}} 6'', as part of Darkwing's distraction.
[[/folder]]

[[folder:Western Animation]]
* In every WesternAnimation/LooneyTunes short where Bugs Bunny dresses as a female to deceive Elmer Fudd, Elmer becomes instantly besotted.
** Played particularly weirdly in ''RabbitOfSeville'': The climactic battle between Elmer and Bugs degenerates into them alternating chasing each other with more and more deadly weapons...until Bugs abruptly comes up with a series of COURTING GIFTS (flowers, chocolates, and so forth, finishing with a diamond ring) and Elmer runs off and comes back in a WEDDING DRESS.
* Used in the ''WesternAnimation/ChipNDaleRescueRangers'' episode "Adventures in Squirrelsitting". Chip 'n Dale not only dressed as a girls, but put on a show in order sneak into Fat Cat's hideout.
* A stock disguise and diversion in the ''WesternAnimation/TaleSpin'' universe, to the point it might overlap with WholesomeCrossdresser:
** 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. [[spoiler: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 [[BarefootCartoonAnimal uncomfortable boots]] as opposed to anything else)
** At one point during "For Whom the Bell Klangs", Louie dresses up as a belly dancer [[WeNeedADistraction as a distraction]].
* Taking a cue from WesternAnimation/LooneyTunes, ''WesternAnimation/AdventuresOfSonicTheHedgehog'' 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 ([[HoYay to Scratch's groom]]), and dressed as a little girl once.
* In ''WesternAnimation/TheFlintstones'' episode "In the Dough", Fred and Barney disguise themselves as women to enter a baking contest when Wilma and Betty get the measles.
* In an episode of ''WesternAnimation/SpongebobSquarepants'' Patrick wrongly thinks someone is threatening him, so he crossdresses so he can stay. HilarityEnsues when ''every'' male character besides Spongebob (who's in on the whole thing) to positively go ga-ga over him. From Mr. Krabbs to Squidward, and Larry the Lobster.
* Bender does this on ''WesternAnimation/{{Futurama}}''. In the episode "Raging Bender" he is forced to wrestle as the Gender Bender, in a tutu and blonde wig. And in "Bend Her", he undergoes a robo-sex change to compete in the Olympics under the name Coilette.
* The ''WesternAnimation/FamilyGuy'' 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 ''Film/MrsDoubtfire'' 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.
* ''WesternAnimation/SouthPark'' examples:
** Mercilessly parodied in "Butter's Bottom Bitch". The police chief dresses as a female whore as part of a sting operation. At least half a dozen guys fall for this, but the police chief takes the operation a step further and actually HAS SEX with the men looking to solicit prostitution. The police chief takes it ANOTHER step further and actually gets married. To his pimp.
** Played more or less straight in "Majorine". The boys discover the girls with a cooty-catcher and believe it to be a future-telling device. In order to steal it, they force Butters to fake his own suicide, dress up as a girl and infiltrate the girls' slumber party.
* Sokka dons the uniform of a Kyoshi Warrior in an early episode of ''WesternAnimation/AvatarTheLastAirbender''. Suki manages to talk Sokka into feeling pretty good about it...until Aang strolls by and compliments him on his "nice dress".
** Made even funnier when you consider Aang's comment earlier in the episode:
-->"Where we're going, you won't need any pants!"
** 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 [[GoneHorriblyWrong vamping in it]].
-->[[BrainBleach ''Helloooo, everybody! I'm Avatar Kyoshi!'']]
** Sokka, at least, [[NeverLiveItDown never quite lives it down]].
*** From a [[DisorganizedOutlineSpeech speech]] explaining his history with the Avatar in front of the entire Black Sun invasion army:
--->"And then we met Suki, who's a Kyoshi warrior. She [[ThatCameOutWrong made me dress like a woman]], and [[DiggingYourselfDeeper then she kissed me]]--" (This was the point where his father stepped in to shut him up, though it took him a few (hilarious) seconds to reach the podium.)
* In an episode of ''WesternAnimation/{{Rugrats}}'', Tommy's Dad and grandfather dressed him up in a dress and a wig to enter him into a baby beauty contest to win a fishing boat. Tommy's mom was not happy.
* Hefty Smurf of ''WesternAnimation/TheSmurfs'' had to disguise himself as Smurfette to protect her from the unwanted affections of a troll king.
* No fewer than three episodes of ''WesternAnimation/ThePerilsOfPenelopePitstop'' had the Hooded Claw do this. In "Cross Country Double Cross", he dressed as an old woman to hitch a ride on Penelope's motorcycle, and in two other episodes he impersonated Penelope herself.
* In ''WesternAnimation/TheProblemSolverz'' episode "K-999 and Da Little Explorerz", Alfe dresses as a girl scout so he can get Nina's missing semaphore badge for her. He changes his name to Alfena, dons glittery makeup, and somehow manages to fool everyone, even though the scouts have a radar that can detect boys in their organization.
* The titular character of ''WesternAnimation/EekTheCat'' 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.
* WesternAnimation/PinkyAndTheBrain are always [[PaperThinDisguise wearing disguises]], and about a third of those involve women's clothes.
* ''Franchise/ScoobyDoo'' examples:
** Shaggy and Scooby are forced to dress as women in the first episode of ''WesternAnimation/ScoobyDooMysteryIncorporated'' so the team can searched a suspicious location that was hiring female workers.
** In two of the Scooby-Doo DVD animated movies, Shaggy is dressed as Daphne and Scooby is dressed as Velma.
** The plot of ''WesternAnimation/ScoobyDooInArabianNights'' centers around Shaggy disguising himself as a harem and then having the Caliph wanting to marry him. Shaggy has to pull a ScheherezadeGambit to get out of the wedding.
* In an early ''ComicStrip/{{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 ''WesternAnimation/ThePowerpuffGirls'', 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 ''[[Franchise/CareBears Adventures in Care-A-Lot]]'' episode "Battle of the Band," Grizzle dons a WigDressAccent 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.
* Gus does this in the final episode of ''WesternAnimation/{{Recess}}'' as part of T.J.'s plan to get their baseball bat from the Ashleys.
* Doowee from ''WesternAnimation/SallyBollywood'' 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 Literature/LittleRedRidingHood, in order to get onstage.
* In the very first episode of ''WesternAnimation/WhatsWithAndy'', [[PrinceOfPranksters 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.
* In ''WesternAnimation/SheZow'', Guy wears a female superhero costume to [[http://vimeo.com/38396064 fight crime and save the day]].
* Timmy in ''WesternAnimation/TheFairlyOddparents'' episode "Operation: Dinkleberg" is dragged into one his Dad's plot in spying on Mr Dinkleberg, and has to deliver a box of pastries with a camera in them dressed as a girl scout.
[[/folder]]

[[folder:Real Life]]
* During the 1973 Operation Spring of Youth, in which Israeli special forces attacked key members of terror organisations residing in Lebanon, unit-commander (and future PM of Israel) Ehud Barak was disguised as a brunette woman.
* In the time of Creator/GaiusJuliusCaesar, 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 [[KarmaHoudini 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 UsefulNotes/TheAmericanCivilWar, 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. [[PaperThinDisguise 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 UsefulNotes/AbrahamLincoln 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.
[[/folder]]

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