1. Nike Air Foamposite One "Royal" 

Year: 1997 

A real game-changer. The molded Nike Air Foamposite One was different from anything Nike had ever done before, different from anything ANYONE had done before. A design intended for Scottie Pippen, but Penny took the sneaker for himself. Eric Avar's design used the best Nike had to offer, from Zoom Air to a translucent outsole to a carbon spring plate. The $180 price point was astronomical at the time — but perhaps appropriate for some shoes that looked like they came straight from a NASA laboratory.