14. Bob Cousy
Significant Sneakers: Converse Chuck Taylor All-Stars, PF Flyers
Bob Cousy was making basketball sneakers cool before most of us were even even a thought in our parent's minds. Cousy's sneaker style may not have included any crazy tech or fancy colors, but back in the day, the real player's let their game speak. PF Flyers even brought back Cousy signatures in recent years to pay tribute to this legendary six-time NBA champ.