Nike Air Up  

Year: 1994 

Player: Penny Hardaway

Nike, listen, we really need these back and they would definitely make it back on the court. While not an official Penny shoe per se, it was the first to feature his number 1 — a beta version of the Penny logo. Nike made Pippen a pair too, but they didn't come close to touching the blue and black nubuck and suede upper of the Pennys.