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A streetwear clothing shop originated in San Francisco, California. Sells clothing, hats, and paintings designed by graffiti and/or street artists such as Jeremy Fisch.

Was once a pleasant, local store where sneakerheads and hipsters visited to pick up some semi-expensive clothing. However, once the word got out it became largely commercialized (in San Francisco) and is now a place where soccer moms come to purchase "cute" jackets for their little kids. Thanks to its commercialization, awkward kids and momma's boys now are running the streets of the Bay Area with Upper Playground's clothing, and its reputation is slowly falling into the gutter.
Awkward Kid: Hey guys, did you see my Upper Playground hat? My mom gave it to me for Christmas!
Ex-fan: Man, I bet you don't even know who designed that hat.
by sneakhead December 29, 2009
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