While it's natural to dig the scoundrel steez of the Barbary Coast, being too historically accurate will leave you caked in dirt and addicted to opium, though still sporting a nice prospector-y hat. To evoke the spirit without looking totally crazy, grab SuperFishal, at Upper Playground
Local artist Jeremy Fish's limited but effective apparel and accessory collection's inspired by Gold Rush days of gamblers, johns, and other standard-bearers of scumbag-chic. Start off by covering yourself with a brown tweed herringbone jacket w/ SF's signature bunny-skull logo and quilted innards to match; round out with a Western-styled premium leather/brass-buckled belt and a matching skull-banded fedora stuck with a plume, for that unf*ckwithable birdwatcher look. Then, give your pocket-lint company with a tin/debossed leather cig case, a brass Zippo affixed with a skull-bunny, and a mini SF-branded Moleskine notebook in which to record dirty deeds, and the fact that your syphilis has reached the Awesome stage
Because 9 out of 10 cops agree that modern crimes are exclusively perpetrated in T-shirts, there're also graphic tees, like "Slow & Steady" (a drunk charioteer drawn by a skull-encased turtle) and "Scooter Geeks": a winged skeleton on a Vespa that unfortunately evokes another excessively crazy San Francisco image, that one Third Eye Blind video. You know, the one with the scooters?