2. Nike Air Force Max — Charles Barkley 

Year: 1993 

Chuck won the MVP award and the sneaker battle against Mike in '93, but that's as far as it went. The Fab Five might have brought the shoe more notoriety but seeing Barkley rock the Air Force Max on the NBA's biggest stage left just as timeless an impression. They were a prequel of what was to come from his highly respected signature series. He's not a role model but you can't help but follow in his footsteps.