Nike Air Pippen II

Worn by: Scottie Pippen, Bill Wennington 

Year: 1998 

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 '50s Mercury inspired side stripe (which also provided support), Zoom Air cushioning, and a sleek cut perfect for the court or with jeans. Bill Wennington, though? He must have swiped a pair from Pip's locker.