At the VMAs last night, Lady Gaga spent the entire evening as her “male counterpart” Jo Calderone (which she first broke out on the September 2010 Vogue Hommes Japan cover, left) vehemently refusing to break character. Perhaps she felt she’d exhausted all womenswear options? Ran out of Versace? Couldn’t get to the costume store because of Irene? (I’m done now).

Whatever the reason, it made us think of some other famous gender-bending moments in fashion. Take a peek at who passed the best as the opposite sex (hint: there’s one designer who really loves his drag).