5. Nike Air Raid — Donald Faison 

Year: 2004 

In the early '90s, strapping up was just a much about the courts as it was the corners. Inspired by street-ball culture, the Nike Air Raid was a favorite in the streets of NYC thanks to its ability to hold up on the blacktop. If you weren't sure what the point of these was, the "FOR OUTDOOR USE ONLY" lettering should have helped you out. Faison wasn't going to let his bromance from Scrubs kill the street cred — good choice, Turkleton.