15. Nike Air Max Penny II

When: 1997

Who: Richard Hamilton 

Before the mask, Rip Hamilton had a lot of pressure to help take over after Jesus Shuttlesworth left campus. In his sophomore season, he took court in Penny's second signature sneaker. The shoes utilized 3M throughout the upper and the branding on the ankle to pop on the hardwood. We can't argue Rip's choice with these — featuring maximum comfort and a close feel to the ground so he could torture opponents on the drive or stop on a dime for a fadeaway jumper.