City-repping gear is a slippery slope -- while showing the love is great, too often you find yourself locked up in "Hotel Alcatraz, 24hr Security, Quaint 9'x9' rooms...". For Frisco-wear that doesn't make you look like you're from Iowa, consult 22Tykoon
Based in the founder's Lower Haight apt, 22's a silkscreen/embroidery operation boasting an extensive online catalog of original Bay-themed graphics, which they'll slap onto made-to-order tees, hoodies, buttondowns, and jackets. Start by picking your image: from the unquestionably local (a streetgrid within a chest-spanning MUNI logo, the skyline as a rabid pit bull's lower jaw), to self-referential hometown-ness like a Jack Daniels logo reading "Bay Area... Quality California Tykoon", to more obscure Yay Area ("The North Face" becomes "The Thizz Face", while Mac Dre floats hy-in-the-phy over the Bay Bridge). Some designs're more random, but still let you brag "This is from an underground SF artist": in "James Bond", Sean Connery looks at you coyly from a harlot-packed hot tub, while "Virgin Mary" has the Virgin of Guadalupe's purity defended by a tank and a paratrooper-dropping helicopter (nice try, but here's $10 that He finds a way to hit it)
Once you've chosen, email the founder: tees just require size and color, while hoodies/buttondowns/ jackets depend on available stock (you're also welcome to bring in your own gear). Pay a little extra for embroidery to accent your graphics, or to have your hoodie lined with repurposed silken textiles -- letting you show love to the necktie without locking yourself up in "Hotel Office".