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

When: 1999

Who: Richard Hamilton 

The Jordan XIVs were another Tinker Hatfield makeup and used inspiration from MJ’s Ferrari 550M to create a fast-looking, lower-cut model. The Ferrari-like badge, air "intakes" in the midsole and the metal tips on the laces added to the high-tech, high-end feel. The shoes debuted super-early in the '98 NBA Finals, and figured big in highlight reels across the nation as Mike hit that famous step back “final shot” against the Utah Jazz. Hamilton's legacy in these aren't that deep but he did get a ring and Most Outstanding Player honors in the XIVs.