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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.