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Wear whatever you want, but no gray. People will judge you by how you play, not what you wear, especially if you go to the same pickup session a few times and get to know people. Personally I'd avoid the Gretzky jersey, but I also wouldn't treat anyone wearing one any differently.
Also, I live in the D.C. area and there are a few guys who wear Caps stuff at pickup. No one cares.
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