When: 1994 

Dads aren't usually seen as the epitome of "rebel style," but Bruce Jenner was doing his best all-black everything rendition in the mid-'90s. Dude wouldn't look out of place in the saddle of a Harley cruiser with his fringed leather jacket. Usually, you don't label a track and field Olympian as someone who could kick your ass, but Jenner knows being stylish is mostly mental swagger, and we can't hate.