66. Nike Air Penny II

Year released: 1996

Complex says: Penny's second signature sneaker didn't quite live up to the Penny I, but it still stood out. The shoes utilized 3M on the lining throughout the upper and the branding on the ankle to pop on the courts. For cushioning you had the Air Max unit in the heel and Zoom Air in the forefoot allowing Anfernee maximum comfort and a close feel to the ground so he could torture opponents on the drive or stop on a dime and drop one to teammates cutting to the bucket. No denying the ripple foam support "wave" and the "Atlantic Blue" colorway which pushes these up to classic status.