Year: 2010
Sneaker: Dolce & Gabbana hightop

Players can-and will-wear virtually anything in an NBA game. Especially in recent years. But no one was prepared when, in the winter of 2010, Gilbert Arenas wore a pair of triple-strapped Dolce & Gabbana hightops in a game against the Lakers. The $395 price tag wasn't particularly shocking (have you ever shopped for Jordans at Flight Club?) but the idea of a professional athlete playing in high-end fashion sneakers was. Even with orthotics. Arenas wore tons of different sneakers in '10-11, but none topped these.