David Bowie
Rock 'n' roll is no stranger to rebellious androgyny (the New York Dolls come to mind). But in the case of David Bowie — whether in Ziggy Stardust–era glam or as the drug-addled skeleton of his '70s funk period — it was always more than a defiant look. It was part of a much bigger creative identity.
Bowie's career can be defined by competing dualisms: aesthetics and sound, masculine and feminine, backward-drawing inspiration and forward-moving reinvention — Lady Gaga before she ever sang a note. That sort of creative friction has been in place for more than 40 years, resulting in everything from Bowie's snaking around in spandex and makeup to his gracing red carpets in head-to-toe Thom Browne.
In many ways, Bowie's looks epitomize the nature of fashion: always at odds with the present, forever evolving.