January 9, 2013 9:05 am

Fifty Most Iconic Gender Benders of All Time

By Aaron Wong

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.

Which is not to discount the transgendered among us who express their identity through their appearance. If anything, trans men and women remind us that clothes are powerful tools for shaping our perceptions of self and of others. In Vested Interests: Cross-Dressing and Cultural Anxiety, Marjorie Garber argues that “transvestism is a space of possibility structuring and confounding culture.” She suggests that cross-dressing challenges “easy notions of binarity” and focuses attention “onto a figure that … incarnates, the margin.”

Ironically, it is this marginality that makes the cross-dresser so central to culture. Because if we are interested in men and women, and in the differences between them, we can’t help but be intrigued by those who defy such distinctions altogether. The fascination with cross-dressing recurs throughout history, from the performative, personal, and political, in culture highbrow and low. From Shakespeare to genderqueer, from Warhol to RuPaul, here are 50 transcendent icons.