Nike Air Up

Year (of Sneaker): 1994 

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. SP's gun-shy off-guard had one of the hottest '90s kicks on while he was dropping more bombs than Flex during a Yeezy debut. Damn Nike, can we please get a proper retro?