Film: What's Eating Gilbert Grape?
Year: 1993
Signature Look: "Derelicte"

True, Arnie Grape's state of uncouthness is explained by a fear of water he develops in the course of the film, but aside from that, he has some truly stylish moments. The yellow button-down with the red hat and tie works without making him look like a McDonald's employee, while the camo T-shirt, hoodie, and washed denim is an outfit you'd still see on dudes running around the streets today.