Episode: #25 'Working it Out'
Year (of Sneaker): Unknown
There is no question that Nike was king when the shoe first kicked off thanks to its Jordans and other high-profile basketball sneakers. When it came to style though, the Three Stripes was just as important to the repertoire. In the final epsiode of the first season Will busts out the slick black adidas boots while he tries to woo Hillary's boss to help her make a good impression.