- 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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- 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.
Film - Animated
- One scene in Robots: while Fender 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.
Film - Live Action
- 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.
- In the Seinfeld episode The Glasses, George is sold a pair of women's glasses made by Gloria Vanderbilt.
- 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."
- 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.
- 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.
- 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 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 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.
- 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.
- 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.
- 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!
- 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.
- In The Jetsons the automatic grooming device(s) would occasionally dress George in Jane's clothes and/or give him her hairstyle.
- Quick Draw McGraw went behind a partition to change into his El Kabong alter ego and emerged in a ballet tutu instead.
- After having his sandals broken, Samurai Jack tries on a pair of high-heel shoes functionally similar to the sandals before being called out by onlookers.
Unfortunate Character Design Administrivia/No Real Life Examples, Please! Unproblematic Prostitution