Brian Chesky: Gucci Ace Leather Low Top Sneaker

Airbnb CEO Chesky is another stylish exec, and often chooses unique — and expensive — footwear. The Ace sneaker has traditionally been a popular model for Gucci, and the brand itself has recently seen a resurgence in the fashion world, according to Flight Club.

"The last and current season has been trending on the blogs and among celebrities," Flight Club says.