The Bacchae by Euripides
Pentheus wants to witness the revels of the Maenads, women under the ecstatic influence of Dionysus who range freely in the woods and mountains. He is persuaded by the god that in order to do this he must dress as a woman. He is spotted spying by the possessed women and is torn to pieces.
Metamorphoses by Ovid
Thetis, Achilles’ mother, knowing that her son will die if he fights in the Trojan war, disguises him as a woman among the daughters of King Lycomedes. Odysseus turns up with some girly presents plus a spear and shield, which are immediately seized by the warrior, who thus reveals himself.
Epicene by Ben Jonson
Rich, grumpy, misogynistic Morose proposes to disinherit his nephew Dauphine by marrying, provided he can find a “silent woman”. A spouse called Epicene is found, and turns after marriage into a perfect shrew. Morose pays Dauphine to rid him of the termagant, whereupon his resourceful nephew pulls off the wife’s wig and reveals her to be a male in disguise.
Don Juan by Lord Byron
In Istanbul, our hero is sold as a slave to one of the sultan’s eunuchs, who commands him to dress as a woman. He has been spotted by the sultana, Gulbeyaz, who has designs on him. When the sultan arrives he rather fancies “the new-bought virgin”. “I see you’ve bought another girl; ’tis pity / That a mere Christian should be half so pretty”.
Jane Eyre by Charlotte Brontë
In a sequence usually omitted in film adaptations, Mr Rochester dresses as an old Gypsy woman and turns up at his own dinner party to read the fortunes of the guests. Even Jane does not recognise him, until he suddenly throws off his disguise.
Huckleberry Finn by Mark Twain
On the run, Huck and escaped slave Jim find some women’s clothes on an abandoned houseboat, and Jim persuades Huck to go ashore disguised as a girl, to find out if people are still searching for them. As “Sarah Williams” he is admitted to a lady’s house, but she sees through his disguise when he begins to forget his own supposed name.
The Story of an African Farm by Olive Schreiner
Farmer Gregory Rose shows his devotion to the rebellious Lyndall by dressing himself in her mother’s clothes in order to serve as her nurse when she is terminally ill. She accepts his disguise and is consoled by his presence.
The Wind in the Willows by Kenneth Grahame
In prison for stealing a car, Toad wins the sympathy of the jailer’s daughter, who dresses him as a washerwoman to help him escape. He wanders the countryside, hitching a lift first on a barge and then in the very car that he earlier stole. Foolishly, its owners let this friendly lady take a turn at driving.
“William the Showman” by Richmal Crompton
William Brown is staging a historical waxworks show with the Outlaws and decides that the poor audience response is down to the lack of “famous ladies”. After a quick raid of sister Ethel’s wardrobe, he struts his stuff as Mary Queen of Scots.
On the Razzle by Tom Stoppard
Rustic apprentice Christopher and his garrulous companion Weinberl travel to Vienna with a hare-brained idea of going “on the razzle”. Hiding from their boss, they end up in Madame Knorr’s women’s clothes shop, where they must don capacious tartan women’s garb and pose as mannequins. More cross-dressing follows. “I’m not the woman you think I am … I’m not even the woman you think is the woman you think I am”.
Full article and photo: http://www.guardian.co.uk/books/booksblog/2011/nov/04/ten-best-men-dressed-women