Ever going to visit San Francisco? If you do and don't want to look like a tourist, wonder over to Haight Street, where all the ex-hippies and Grateful Dead heads lives (you can even visit their homes - Joplin, Grateful Dead, Hendrix, etc). The area has awesome stores like True, Stussy and other urban street wear for your closet. Just be nice to the bums - one whipped out an iPhone on us.
Oh and avoid the Tenderloin district. Sketcccccchy (Jones St. that is), unless you want to buy crack at 1 in the afternoon from a man in a wheelchair.
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