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In fiction
Women dressed as men, and less often men dressed as women, are a common trope in fiction. These disguises were popular in Gothic fiction, such as by Alexandre Dumas, Charles Dickens and Eugène Sue, and also appear in a number of Shakespeare's plays. In Norse myth, Thor disguised himself as Freya. In The Wind in the Willows, Toad dresses as a washerwoman, and in Lord of the Rings, Éowyn pretends to be a man.

In science fiction, fantasy and women's literature, this literary motif is occasionally taken further, with literal transformation of a character from male to female or vice versa. Virginia Woolf's Orlando: A Biography focuses on a man who becomes a woman, as does a warrior in Peter S. Beagle's The Innkeeper's Song; while in Geoff Ryman's The Warrior who Carried Life Cara magically transforms herself into a man.

Other popular examples of gender disguise include Madame Doubtfire (published as Alias Madame Doubtfire in the United States) and the movie adaptation Mrs. Doubtfire featuring a man disguised as a woman. The movie Tootsie features Dustin Hoffman disguised as a woman. Furthermore, Madame Butterfly (play) features a male spy passing as a female Japanese actress.