Character: Arnold from Hey Arnold!

P.S. 118's very own may have represented the fictional city of Hillwood, but parts of it definitely resembled New York City. Sure, Gerald kept it fresh in a football shirt and flat top, and even Stoop Kid held his own with a grunge-inspired look, but Arnold really had a lock on his style. Tiny caps may have never made it big, and sure, his awkward side part might've been borrowed from Wolverine, but when your super-long flannel gets co-signs from A$AP Rocky and Yohji Yamamoto, you're pretty much a style icon.