27. Nike Air Trainer 1 "Draft Day"
The Air Trainer 1 is a classic and when you throw premium materials (ostrich-skin at that) and a tasteful color combo, it's hard to deny greatness. The black and almost-but-don't-call-it-Infrared combination is almost as classic as the Trainer 1 itself, we're just used to seeing it on the Air Jordan VI. This is one you'll wish you didn't miss.