20. Big Boi — Air Jordan III "Black/Cement"
When: Mid '90s
Outkast started as some kids being gangstas, and they had the Caddys and the Lexuses to prove it. And long before they became known for their fashion game (admittedly, Dre more than Big Boi), the young Antwan André Patton saw nothing wrong in mixing an adidas Equipment t-shirt with some Js. Well, at least they were real.