- 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
Anime 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 got upset with them. Film - Animated
- One scene in Robots: while Bender 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.
- 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 a pair of Lisa's panties after they spend the night together.
- 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. 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 (UK) 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 epsiode of Frasier Martin has to start wering 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.
- 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.
- In The Jetsons the automatic grooming device(s) would occasionally dress George in Jane's clothes and/or give him her hairstyle.
Hello, Unknown Troper. You'll need to get known to lend a hand here.