Jon Warren 

Company: Vans 

Significant shoes: Rowley XL2, Escobar, TNT II

As the head of footwear design classics over at Vans, Jon Warren didn't design all of Vans's all-time classics, but he played a large role in bringing back favorites and making others better. And before he was put in charge, he earned his (side) stripes by designing signature product for a mess of pro skaters. Fickle bunch.