When: 1995 

Pulling your swishy track pants up to your man boobs is never the move, but Bruce Jenner has zero fucks to give, 'cause he's chilling at Disney World. But he still looks cool wearing a monochromatic 'fit—it's an easy way to tie together your ensemble and it doesn't take too much thought. Plus, check the dude's steez next to him, it sucks (except for the kicks). Jenner wins again.