01/11/2013 11:05 am ET

Fifty Most Iconic Gender Benders Of All Time

Admit it. You’ve dabbled. We all have. Whether it’s guyliner or a boy and his murse, a woman’s tomboyish crop or her biker jacket and boyfriend jeans — there’s something undeniably chic about gender-bending style. We’re captivated by androgynous women like Stella Tennant and Tilda Swinton, and swoon for brooding pretty boys like Justin Bieber and James Franco. Because getting dressed always involves a bit of role-play — and sometimes the most intriguing role happens to be a different sex.

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