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Unplanned Crossdressing

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When I awoke next mornin', I had an achin' head.
My gold watch and my pocketbook and the lady friend had fled.
Now looking round this little room, nothin' could I see
But a woman's shoes and apron, which now belonged to me.
Now dressed in the lady's apron, I wandered most forlorn
Till Martin Churchill took me in and he sent me round Cape Horn.
New York Girls, folk song
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Under ordinary circumstances, Adam wouldn't opt for women's clothing, but through a series of misadventures or a matter of misunderstanding, he puts on an outfit intended for Eve. In some instances, he might not even realize he's wearing women's clothing until someone else points it out to him.

It's obviously Played for Laughs — he's not intending to pass as female, the goal isn't to disguise himself, and it's not a habit, wholesome or otherwise. The viewer can assume that after the incident Adam won't be delving back into ladies wear any time soon.

Compare Dragged into Drag when the guy is forced into it. Contrast Disguised in Drag when the guy does it to hide (or to sneak into a women's only area).

Related to Gravity Is a Harsh Seamstress.


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Examples:

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    Anime & Manga 
  • In Super Dimension Fortress Macross, 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.

    Comic Books 
  • 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.

    Comic Books 
  • Douwe Dabbert: 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.
  • Lori Lovecraft: 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.
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    Comic Strips 
  • One Beetle Bailey strip had Beetle Waking Up Elsewhere after sleeping in the back of a truck, and having nothing with him but his underwear and a blanket. He calls Ms. Buxley and asks to borrow some clothes, and shows up wearing one of her dresses when he returns to Camp Swampy.

    Films — Animation 
  • A variation in Robots: while Fender 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.

    Films — Live-Action 
  • Combined with Rummage Sale Reject in 68 Kill. 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 Bringing Up Baby, David Huxley ends up wrestling a leopard in the middle of a pond. Soaking wet and filthy, he returns to Susan Vance's home where she loans him her very girly robe while his clothes dry out. Susan's aunt, Elizabeth, is less than impressed with his wardrobe choices.
    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 Danny Kaye 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 Weird Science, Wyatt absentmindedly puts on Lisa's panties after they spend the night together.

    Literature 
  • In one The Machineries of Empire short story, after escaping from a Gwa prison, Jedao knocks out the first person he encounters to obtain some clothing that would let him slip undetected. Unfortunately for his stress level, this happens to be a woman.

    Live-Action TV 
  • The pilot episode of Being Human 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.
    Mitchell: Nice blouse.
  • Mentioned but not shown in an episode of The Big Bang Theory. 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!
  • An example in The Drew Carey Show: During a brief period when Kate and Oswald were Friends with Benefits, 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.
  • In an episode of 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.
  • 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.
  • Gossip Girl (2021): Julien and Zoya improvise to dress up as the real boyfriends of the women who their female friends are cosplaying as after their initial choices were leaked before, so they're still original.
  • A recurring joke in How I Met Your Mother is Ted's red cowboy boots, which are apparently women's. This is never discussed around him so he doesn't know.
  • In an episode of The Odd Couple, 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.
  • In an episode of 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."
  • In the Seinfeld episode "The Glasses", George is sold a pair of women's glasses made by Gloria Vanderbilt.
  • 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 available garments, which are women's clothes but in their sizes.
  • In The Young Ones, Neil ends up in a dress after he fell out the bathroom window and his room was nailed shut. He raided Rick's room and found only a dress with Rick's nametag on it.

    Music 
  • 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.
  • 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.

    Radio 
  • Our Miss Brooks: In "Dress Code Protest", a series of mix-ups results in Miss Brooks wearing Mr. Conklin's pants after tearing her skirt and being unwilling to go about in a borrowed pair of Harriet's gym bloomers. Mr. Conklin had pushed his pair of pants through the transom, telling Stretch Snodgrass to get them cleaned. However, Stretch had left leading Walter to find them and take them to Miss Brooks. This leaves Mr. Conklin is stranded in his office with no pants, and only Miss Brooks' torn skirt.

    Video Games 
  • Lei spends all of Death Smiles II in an Elegant Gothic Lolita maid outfit, because it was the only thing available when he arrived and the alternative was hypothermia.
  • Sometimes this will be the case when you switch to Trevor in Grand Theft Auto V, as he'll wake up confused and hungover in a random location in San Andreas, wearing a dress, the implication being that he got up to some manner of drunken mayhem while you were controlling one of the other protagonists.

    Web Animation 
  • 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?

    Web Comics 

    Web Videos 

    Western Animation 
  • In The Amazing World of Gumball episode "The Dress", Gumball is forced to wear his mom's wedding dress to school because his father shrunk all his clothes in the wash. When he's inevitably spotted by the other kids, they don't recognize him, and in fact, they're all smitten with him except for his sister Anais (even the girls, Miss Simian, and his own brother).
  • In The Harlem Globetrotters episode "Bad News Cruise", Curly Neal falls through the main deck into a pile of women's clothes, and emerges dressed like a woman.
  • House of Mouse: 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 The Jetsons, the automatic grooming device(s) would occasionally dress George in Jane's clothes or give him her hairstyle.
  • Quick Draw McGraw once went behind a partition to change into his El Kabong alter ego and emerged in a ballet tutu instead.
  • Samurai Jack: After having his sandals broken, Jack tries on a pair of high-heel shoes functionally similar to the sandals before being called out by onlookers.

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