The Fresh Prince's 25 Greatest Outfits

5. Varsity Jacket and Flannel Shirt Tied Around The Waist 

Episode: 81 

In season four Will continues to mature the style and the loud colors started to die down. During a power struggle acting like Ashley's protective older brother we get a shot of Will in a fitting grey and black varsity jacket and a flannel tied around his waist. Twenty years later, numerous rappers have been rocking the same exact thing

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