21. Eric Koston

Complex says: One of the most influential skaters of all-time, Eric Koston has been sponsored since '93, got his first signature kicks in '97 and this past year he teamed up with Nike for his own SB model. While this may have come as a surprise to some, Koston was down with the Swoosh long before he signed on the dotted line. Even before he got on Nike he was building a collection that was heavy on the Jordans (which inspired some of his later signature models). A huge Los Angeles Lakers fan, Koston proudly let his NBA influence shine through. Wearing your own sneakers has to be like listening to your own music though, eventually it gets old and you might be taken as an egomaniac for it. Hardly an issue for Koston since he diversifies his sneakers with a crazy mix of Jordans, Nike SBs, Vans, and he even messes with Gucci.