Air Jordan XV

Released: 1999
Complex Says: "What's the best way to make a sneaker look like it's ready for war? Well, one can start by hooking it up with a woven Kevlar upper and a design inspiration from NASA's futuristic experimental X-15 rocket plane. But, despite its military foundations, the post-Jordan era XV was also luxuriously equipped with Italian styling reminiscent of the Prada 'America's Cup'. These contrasting factors – along with a tongue that many believe emulated Jordan's facial expression when attacking the rim — made the XV a 'hate it or love it' kind of shoe."