Year: 1996
Sneaker: Nike Air Choad

Everyone remembers the success of Nike SB, built on the back of the re-issued Dunk, but not nearly as many people remember Nike's first attempt at entering the skateboarding market. This was five years earlier, and Nike tried to do it strictly via new performance models, including the Air Choad and the Air Snak. This didn't go over well with skateboarders—or pretty much anyone else.