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i don't play ball, baby
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you never run into dress code issues in nice bars, clubs, or restaurants in Boston? i'm in NYC and sneakers are a non-starter in just about all upscale clubs/lounges.
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i've gone to quite a few "chic" or "swanky" spots in NYC and had no problem getting in wearing black or grey skate shoes. The only place I've been hassled is in Vegas (Studio 54), but everywhere else didn't mind (i think you can go in a wife beater and boxers if you're paying for bottle service).
Somewhat similar:
