Rapper: Eminem

Eminem is far from a hip-hop style icon, but there was a time when that creepy old-ass looking dude getting good pussy in high school was wearing a Shady LTD cap or hoodie. Beyond Shady LTD, Eminem also managed to produce some of the illest Air Max collabs of all time, but sadly many of them remain unobtainable grails since you had to cop them via auction.