Whether it's Weezy's codeine-carrying entourage or Adrian Grenier's...losers, it's best to roll with your homies when entering uncertain territory. Rumbling into New York, Upper Playground.

The SF brand's first East Coast foray, UPG's a sartorial clearinghouse for all manner of gear graffers, taggers, and bombers -- street artists who, not content with marking buildings, now territorially piss on you. Starting with their eponymous line, UPG hawks tees and hoodies commissioned from illustrators like Munk One (a blinged-out Biggie-esque walrus), sketch artist N8 Van Dyke (a walrus-masked bank robber), and Christopher Wright, whose tee (smoking twentysomething framed by wreathed shield) perfectly captures the L-Train zeitgeist with its caption "Demented and Sad but Social". UPG also slings slick gear from their Fifty24SF "showcase brand" (created by artists like Morning Breath, Lude Behavior, etc), plus three sub-lines: Jeremy Fish's skull & furry creature-themed superFishal; Sam Flores' despondent-cartoon 12Grain; and Estevan Oriol's "Oriol" -- gritty photos of AK-toting thugs, stacks of $100 bills, and Latinas flashing what you'll assume are gang signs, but might just be shows of support for the Cal Golden Bears.

UPG also purveys photography books and arted-up accessories, like backpacks, throw pillows, and beer mugs -- because when entering uncertain territory, it helps to be drunk.

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You can also buy online at UpperPlaygroundStore.com