1. Air Jordan XIV "Last Shot"

Originally Released: 1998

Complex says: Let's forget for the moment that Michael Jordan hit one of the biggest shots in NBA Finals history while wearing this model and focus solely on the shoe itself. The Air Jordan XIV was designed based on Michael's then brand-new '97 Ferrari 550 Maranello, and the black/red colorway was the most Ferrari-like of them all. Sleek, fast, exotic. One to end on.