History Main / UnplannedCrossdressing

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Related to GravityIsAHarshSeamstress.

* ''Series/{{Friends}}'': Phoebe and Rachel take Ross clothes shopping. Ross accidentally ends up with one of Rachel's bags and wears her shirt, not realizing it's a women's style. Joey tries to point it out, but Ross doesn't get it. Then Ross's date shows up wearing the exact same outfit.

** In the episode where Joshua is introduced, he describes losing most of his stuff in a fire and having only a suit and a skirt left. He acknowledges the suit looks great, but it wasn't fun having to wear the skirt to the dry cleaners in order to drop the suit off.

* ''Series/{{Friends}}'': Phoebe and Rachel take Ross clothes shopping. Ross buys an ensemble that he adores. No-one can convince him that it's actually women's wear. No-one except his date who shows up wearing the exact same outfit.

* In a picture-book example, in Axel Scheffler's "The Little Puddle" in the ''Series/PipAndPosy'' series, Pip ([[a boy bunny Funny animal]]) has a potty accident when playing at mouse Posy's house and wets his trousers. Posy gives him a dress to wear. As they're implied to be preschool-aged, nothing is made of this.

* ''Series/MrBean'' was locked out of room 426 while naked. He eventually finds woman's drag to conceal the nakedness and reach the consigliere for the room key. However, another actor approaches and says that's his prop and rips off the earring.

* In an episode of ''Series/{{Frasier}}'', Martin has to start wearing glasses. He finds a pair he really likes, and no-one has the heart to tell him they're women's frames.

* In ''WesternAnimation/TheAmazingWorldOfGumball'' episode "The Dress", Gumball is forced to wear his mom's wedding dress to school because [[{{Manchild}} his father]] [[ShrunkInTheWash shrunk all his clothes in the wash]]. When he's inevitably spotted by the other kids, they don't recognize him, and in fact, [[AttractiveBentGender they're all smitten with him]] except for his sister Anais ({{even the girls|want her}}, [[SadistTeacher Miss Simian]], and ''his own brother'').

[[folder:Comic Books]]
* ''ComicBook/DouweDabbert'': Happens to Domoli in "The Black Kimono". When visiting Japan, Domoli and Douwe are given Kimonos to wear because their regular clothes are being washed, but Domoli is accidentally given a woman's kimono. And since he doesn't know the difference between the two, he puts it on anyway. Fortunately for him, Pief quickly points out the mistake.
* ''ComicBook/LoriLovecraft'': In ''The Big Comeback'', Lori and R.C. are attacked by a demon immediately after having sex. R.C. leaps to his feet and tanks on the first item of clothing he manages to grab, which happens to be Lori's panties.
[[/folder]]

* ''Manga/{{Doraemon}}'': as Nobita and Doraemon go back in time to look for a girl the former's father had a crush on, the former gets his clothes soaked and the only dry outfit available for him to change into is a dress. It turns out Nobita in this outfit ''is'' the girl his father had a crush on.

* A variation in ''WesternAnimation/{{Robots}}'': while Fender [[spoiler:is trying to escape the chop shop]], his legs fall off. He tries carrying on without them until he finds some legs that fit him. Said legs are female.

* There's an old sea shanty from the late 1800's called "New York Girls", in which a sailor spends the night with a hooker, only to find out in the morning that she's robbed him of everything he owns including his clothes. He's forced to don her clothes to return to his ship.

Compare DraggedIntoDrag when the guy is forced into it.

%% The examples have been alphabetized. Please put any new example in its proper place in the folder rather than at the end.

* One Punisher villain was a mob boss who escaped Frank by fleeing through a women's clothing store and hurriedly disguising himself, and then lived a quiet life as an unassuming widow for a while.

[[folder:Films -- Animation]]

[[folder:Films -- Live-Action]]

* ''ComicBook/DouweDabbert'': Happens to Domoli in "The Black Kimono". When visiting Japan, Domoli and Douwe are given Kimonos to wear because their regular clothes are being washed, but Domoli is accidentally given a woman's kimono. And since he doesn't know the difference between the two, he puts it on anyway. Fortunately for him, Pief quickly points out the mistake.
* ''ComicBook/LoriLovecraft'': In ''The Big Comeback'', Lori and R.C. are attacked by a demon immediately after having sex. R.C. leaps to his feet and tanks on the first item of clothing he manages to grab, which happens to be Lori's panties.

* In an episode of ''Theatre/TheOddCouple'', Felix has a bandage over his eyes due to recent surgery. When Oscar throws him out, he stumbles to the closet and puts on what he thinks is his coat, but is actually his ex-wife Gloria's.

* ''Series/{{Soap}}'': In the Season 4 premiere, Burt and Danny have been drugged and placed in a compromising situation for purposes of blackmail. When they regain consciousness in a sleazy motel, they are in bed wearing lingerie. To get out, they have to put on the only avaible garments, which women's clothes.

* In ''Anime/SuperDimensionFortressMacross'' a group of Zentradi spies sneak aboard the Macross and find human clothing to wear as disguises. Unknown to them, they had stolen women's clothing and walked around town that way until people started laughing at them. Two of them were wearing fairly unisex clothes, but Warera had had the misfortune of picking out a dress.

* ''ComicBook/DouweDabbert'': Happens to Domoli in "The Black Kimono". When visiting Japan, Domoli and Douwe are given Kimono's to wear because their regular clothes are being washed, but Domoli is accidentally given a women's kimono. And since he doesn't know the difference between the two, he puts it on anyway. Fortunately for him, Pief quickly points out the mistake.
* ''ComicBook/LoriLovecraft'': In ''The Big Comeback'', Lori and R.C. are attacked by demon immediately after having sex. R.C. leaps to his feet and tanks on the first item of clothing he manages to grab; which happens to be Lori's panties.

* One scene in ''{{WesternAnimation/Robots}}'': while Fender [[spoiler:was trying to escape the chop shop]], his legs fell off. He tried carrying on without them until he found some legs that fit him. Said legs are female.

* Combined with RummageSaleReject in ''Film/SixtyEightKill''. Chip has all of his clothes stolen and is forced to dress from the contents of the motel's lost and found box. He ends up wearing pink flip-flops, grey sweatpants, and a woman's off-the-shoulder t-shirt with a red lip pattern on it.

* In the ''Series/{{Seinfeld}}'' episode "The Glasses", George is sold a pair of women's glasses made by Gloria Vanderbilt.
* In an episode of ''Series/{{The Office|US}}'', someone tells Michael he's wearing a woman's suit. Michael denies it vehemently, but eventually admits that he bought the suit from a sale bin, not realizing it was a suit for women. (He assumed the peculiarities of the suit -- such as a lack of pockets and buttons on the wrong side -- were because the suit was "Italian.") Later -- as he's complaining about his day -- he says "Also, I accidentally crossdressed."
* ''Series/{{Friends}}'' has a similar example. Phoebe and Rachel take Ross clothes shopping. Ross buys an ensemble that he adores. No one can convince him that it's actually women's wear. No one except his date who shows up wearing the exact same outfit.

-->'''Mitchell''': Nice blouse.

* In an episode of ''Series/{{Frasier}}'' Martin has to start wearing glasses. He finds a pair he really likes, and no one has the heart to tell him they're women's frames.

* In an episode of ''Theatre/TheOddCouple'' Felix has a bandage over his eyes due to recent surgery. When Oscar throws him out, he stumbles to the closet and puts on what he thinks is his coat, but is actually his ex-wife Gloria's.
* An example in ''Series/TheDrewCareyShow'': During a brief period when Kate and Oswald were FriendsWithBenefits, their hurry to redress after spontaneous sex results in Kate in Oswald's shirt and Oswald in Kate's obviously smaller, obviously girly T-shirt.
* Mentioned but not shown in an episode of ''Series/TheBigBangTheory''. Bernadette says Howard had a bad day because he accidentally put on a pair of ''her'' skinny jeans instead of his, but that he has no room to complain: they were actually looser on him than they are on her!

* There are several variants of this, ''Patrick Street'' being the best-known. In the New Zealand version, a miner realizes the hooker was a ''man'' who stole his clothes because he had nothing else to wear -- but left behind a razor so the miner could better disguise himself in his new dress.

'''Port:''' And that wasn't even the best part! ''[places his leg up on the table]'' "Like what you see?"

* ''WebComic/BobAndGeorge'': During one of the MilestoneCelebration parties, a male character was seen wearing [[Anime/NeonGenesisEvangelion Asuka Langley Sohryu]]'s [[SensualSpandex plugsuit]]. He didn't seem to be aware of the problem, and only said it was "[[ComicallyMissingThePoint the most popular cosplay outfit this season]]".

* In ''Webcomic/{{Spacetrawler}}'', Choan [[DestructoNookie accidentally shredded Dimitri's clothes]], so Dimitri later [[http://spacetrawler.com/2010/09/12/spacetrawler-75/ has to make a daring escape in one of her dresses]]. Dimitri is not at all bothered by this ([[UnusuallyUninterestingSight neither is anyone else]]).

* In ''WesternAnimation/TheHarlemGlobetrotters'' episode "Bad News Cruise", Curly Neal falls through the main deck into a pile of women's clothes, and emerges dressed like a woman.
* ''WesternAnimation/HouseOfMouse'': Twice in the short "Donald's Shell Shots", Donald chases Baby Shelby around a department store and goes through the women's clothing section, resulting in Daisy spotting him wearing a dress.
-->'''Daisy:''' So, ''this'' is what you do in your spare time!
* In ''WesternAnimation/TheAmazingWorldOfGumball'' episode "The Dress", Gumball is forced to wear his mom's wedding dress to school because [[{{Manchild}} his father]] [[ShrunkInTheWash shrunk all his clothes in the wash]]. When he's inevitably spotted by the other kids, they don't recognize him, and in fact, [[AttractiveBentGender they're all smitten with him]] except for his sister Anais ({{even the girls|want her}}, [[SadistTeacher Miss Simian]], and ''his own brother'').