19. Lugz Quarter-Zip Sweatshirt, Jeans, and Nike Air Max 95s 

Episode: 147 

Large branding wasn't cool until the show was almost a wrap. The quarter-zip red, white, and blue quarter-zip stayed true to Will's Philly ties. The Air Max 95 is usually ranks atop most runners best of lists. In the second-to-last episode, Will busts them out during a family meeting. The design on these were really a step up from a lot of the Nikes at the time with extra details.