7. Nike Air Penny II "Black/White-Varsity Royal"
Year released: 1996
The Penny IIs were a straight-up masterpiece. Check that flowing support wing, the reflective 3M hits on the piping and the ankle patch, even the way the white midsole made the black upper pop. Combine that with the classic Nike Basketball cushioning system — Zoom in the front, Max in the rear — and this was a sequel that was tough to beat.