WHO: New York (Giants) vs Boston (Patriots)
These two cities are big rivals when it comes to any sports teams, but we're talking about style here. Boston has cool shops like Bodega, Johnny Cupcakes, and Karmaloop, and the New England city is responsible for preppy fashion. Unfortunately, Boston is also notorious for being the worst-dressed city. New York on the other hand, is in its own world when it comes to style. 5th Ave, Fashion Week, the best designers, and streetwear empires all reside in New York.
WINNER: Giants. New York is the style capital, period. If anyone was keeping style scores against NYC and Boston, it would be a blowout.