6. Lil Wayne
Sneakers: Supra, adidas Originals by Jeremy Scott, snowboard boots
Lil Wayne may have the most un-traditional style we've ever seen but there is no doubt, he hepled put Supra on the map. We may never rock snowboard boots courtside like Weezy, but he's definitely made us take a closer look at the Supra Skytop. Not to mention the over-the-top designs from Jeremy Scott's adidas Originals line that Wayne helped take from absurdity to possibility. But for everyone's sake, fur-covered snowboard boots is a step past where the line should be drawn.