17. Lil' Wayne
Ok, Weezy's had his fair share of slip-ups (leopard print jeggings, moon boots, and more recently — snowboard boots at a Lakers game), but he's also had his more stylish moments. Take his Grammy outfit for example: a cardigan, proper pants, and some killer footwear. He's also a big proponent of camo and all-over prints, and we can't fault him for that.