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Vintage Photos of Pop Culture Icons in Drag

Cross-dressing, whether for pleasure or for mischief (or for plays or films), is no new phenomenon. Every little child experiments with putting on the opposite gender’s designated garb, all on-stage women in Elizabethan theatre were played by men, and many people of both sexes have dressed in drag for a variety of reasons, from personal to professional. So why should our pop culture icons be any different? Click through to join in our celebration of drag in all its forms, and see some of our favorite musicians, artists and writers (though by no means a complete selection — we couldn’t find any photos of J. Edgar Hoover) indulging in a little cross-dressing from as far back as 1910.

Virginia Woolf and her friends dressed as Abyssinian dignitaries (she’s the one on the far left), 1910.