4. Nike Air Up "Black/White-Royal Blue" 

Year released: 1994 

This is our unofficiamany of the retro drops we have seen over the past five years. 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.