History Main / UnplannedCrossdressing

-->'''Daisy:''' [[GettingCrapPastTheRadar So,]] ''[[GettingCrapPastTheRadar this]]'' [[GettingCrapPastTheRadar is what you do in your spare time!]]

* ''Knock on Wood'' features Creator/DannyKaye as a ventriloquist who has a few embarrassing run-ins with a woman. He ends up putting on her robe and slippers several times in his confusion. Each time, she has to stop him before he leaves.

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* 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.

[[quoteright:270:[[Film/BringingUpBaby https://static.tvtropes.org/pmwiki/pub/images/bringing-up-baby_3069.jpg]]]]
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* 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 (yes, {{even the girls|want her}}, [[SadistTeacher Miss Simian]], and ''his own brother'').

[[folder:Web Original]]

* ''WebAnimation/{{RWBY}}'': In volume 4, Taiyang and two of the Beacon professors tell a story from when they were students about Tai tricking Qrow into wearing a skirt. Apparently, Qrow decided to roll with it and started flaunting his appearance to the girls.
-->'''Taiyang:''' Hey, all the girls said he had nice legs; I was doing the jerk a favor!\\
'''Port:''' And that wasn't even the best part! ''[places his leg up on the table]'' "Like what you see?"

* 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 ([[AttractiveBentGender in fact, most are quite smitten with him]]).

* 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 (hilariously, [[UnusuallyUninterestingSight neither is anyone else]]).

->'''Daisy:''' [[GettingCrapPastTheRadar So,]] ''[[GettingCrapPastTheRadar this]]'' [[GettingCrapPastTheRadar is what you do in your spare time!]]

-->'''Taiyang''': Hey, all the girls said he had nice legs, I was doing the jerk a favor!\\
'''Port''': And that wasn't even the best part! ''[places his leg up on the table]'' "Like what you see?"

* In ''WesternAnimation/TheJetsons'' the automatic grooming device(s) would occasionally dress George in Jane's clothes and/or give him her hairstyle.
* WesternAnimation/QuickDrawMcGraw went behind a partition to change into his El Kabong alter ego and emerged in a ballet tutu instead.

* 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.

-->''When I awoke next mornin', I had an achin' head.\\

[[folder:Anime]]

[[folder:Film - Animated]]

[[folder:Film - Live Action]]

-->'''Mrs. Random''': Well who are you?\\
'''David Huxley''': I don't know. I'm not quite myself today.\\
'''Mrs. Random''': Well, you look perfectly idiotic in those clothes.\\
'''David Huxley''': These ''aren't'' my clothes.\\
'''Mrs. Random''': Well, where are your clothes?\\
'''David Huxley''': I've ''lost'' my clothes!
* ''Knock On Wood'' features Creator/DannyKaye as a ventriloquist who has a few embarrassing run-ins with a woman. He ends up putting on her robe and slippers several times in his confusion. Each time, she has to stop him before he leaves.

* 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/TheOfficeUS The Office]]'', 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.

* 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.

* 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.

** 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.

* When first introduced in [[http://thewretchedoneswebcomic.com The Wretched Ones]], Jackson is assumed to be a woman due to wearing a woman's cloak.

* QuickDrawMcGraw went behind a partition to change into his El Kabong alter ego and emerged in a ballet tutu instead.
* After having his sandals broken, SamuraiJack tries on a pair of high-heel shoes functionally similar to the sandals before being called out by onlookers.
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* The pilot episode of ''Series/BeingHuman'' finds George, the werewolf, waking up the morning after a full moon. He's naked, so he grabs the first clothes he can find -- from a clothesline. The style isn't exactly flattering.

* In an epsiode 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.

* When first introduced in [[http://thewretchedones.smackjeeves.com The Wretched Ones]], Jackson is assumed to be a woman due to wearing a woman's cloak.