Brian Chesky, Joe Gebbia, and Nathan Blecharczyk

It turns out that all three cofounders of Airbnb have a strong sneaker game. At Airbnb Open in 2016, Chesky (left) wore SeaVees Maslon Desert Boot Wintertide, Gebbia (center) wore Reebok Pump Omni Lite, and Blecharczyk (right) wore Nike Free Trainer 5.0 V6.

Prices: $54, down from $108 (L), $119.99 (C), $89.99, down from $99.99 (R)