38. Air Jordan II "White/Red"
Original Release: 1987
Sports Illustrated dedicated an entire sidebar to Michael Jordan's Air Jordan IIs — headlined "Leapin' Lizards" in reference to both the faux iguana side panels and the then-startling $100 retail price. Made in Italy, the Air Jordan II represented the pinnacle of luxury sports, Gucci in everything but name. Take that, Dapper Dan.