When: 1980 

Look, we admit that we're fans of playing with proportion. It's as simple as wearing short trousers with a long shirt layered underneath a hoodie. But Jenner's Daisy Dukes and belly shirt looks like he stole his girlfriend's clothes. We're all for unisex styles, but a dude should never have to worry about his junk poking out his jorts. Who wears short jorts? That would be Bruce Jenner.