5. Nike Air Challenge LWP
The Nike Light Weight Performance (LWP) push in the mid '90s was incredibly successful on the basketball court, and when it comes to tennis, well, MJ approved, so that's a pretty good co-sign. This is one of those models we'd love to see retro but wouldn't be mad if it remained locked away in elusiveness either. We can only assume Agassi took the LWP approach to heart, considering he cut off his famous hair about the same time he slipped these on.