Aired: 1990-1996

Is there any other choice for the top spot? Sure, barring guest stars and Jazz, Will is the only truly stylish person on the series amongst the super-prepped out Banks family (although latter-series Ashley was pretty fly, too). But the Fresh Prince is really all you need, especially when the freshness lives up to the self-proclamation. His influence is only given more weight today, since fashion is cyclical and you have dudes matching their Retro Js with the loud outfits Will used to sport when he took over Cali, or citing his style in court in the People vs. the Male Crop Top.