69. Nike Air Pippen II
Year Released: 1998
Complex says: Mike wasn't the only one in the Windy City getting blessed with footwear from Beaverton, Oregon. Scottie was known for having his own heat throughout Chicago's title runs but it was his second signature kick that stood out the most. The Aaron Cooper designed Pippen IIs featured a well-constructed tumbled leather upper, a custom Mercury inspired side stripe (which also provided support), Zoom Air cushioning, and a sleek cut perfect for the courts or the streets.