Nike Air Max 2 Trainer 

Episode: #100 'The Client: Part 1', #110 'Will Steps Out', #113 'It's a Wonderful Life', & #115 ' A Decent Proposal'

Year (of Sneaker): 1994

This was Will's go to-shoe in season five. Around this time the lines on a shoe were all the rage for aesthetic pleasure. The Max 2 Trainers are a classic that saw a lot of re-release love in 2011. Will rocked these when he tried helping Ashley launch her music career as well as proposing to his girlfriend (played by Nia Long) after getting shot up taking a bullet for Carlton. Not sure you could file that under: Menace II Society status — but we can't blame NBC for trying to gain a little street cred.