8. Nike Air Flight One "Orlando" 

Year released: 1995 

One. Eastbay didn't really have to put this dude's picture next to the product for you to know who was pushing these kicks. Before Anfernee's first official "Penny" shoe, he laced up in the Air Flight Ones — and the sneakers were so comfortable and the design was so on point then even His Airness donned a pair when he matched up against the Magic and the new up-and-coming face of the league.