2. Air Jordan XIV "White/Black-Varsity Red"

Originally Released: 1998

Complex says: The first official retail version of the XIV, the first "white/black-varsity red" colorup utilized an uncommon mix of materials and colorblocking, matching a black suede toebox with a black tongue and laces, set off by a clean white upper. The forefoot "teeth" were pronounced — and tacky to the touch. No traction problems here.