Marlene Dietrich
The German-born film legend (pictured here in a still from Morocco) was among the first women to look sultry in a suit.
Katharine Hepburn
The tomboyish Pat and Mike star (she was Pat) made trousers a trademark early in her career, revealing a rebelliousness that lasted a lifetime.
David Bowie
Ziggy Stardust was one of many onstage alter egos that allowed Bowie to unleash his inner andro rock god (and love of dramatic shoulder padding).
Diane Keaton
Keaton was so enamoured with Annie Hall’s signature bowler hats and neckties that she still sports the look 35 years later.
Grace Jones
No, Beyoncé, this is fierce.
Tilda Swinton
The puckish actress has said she would “rather be handsome for an hour than pretty for a week.” Presumably she’s okay being both.
Kanye West
Yeezy got ribbed by fellow rappers after sporting a black leather skirt by Givenchy. Shockingly, he did not react well.