In a city charmed by all things retro, the North Beach neighborhood is the place for Prohibition-era fashion (followed by speakeasy-style drinking, of course).
Stop by the Goorin Bros. Hat Shop for the kind of boutique shopping experience from the days of Bonnie and Clyde. It's a shop made for lingering; you're encouraged to try on anything and explore the nooks and crannies of the well-curated space (make sure to check out the cinema chairs upstairs).
Started in 1895 and headquartered in San Francisco since 1949, Goorin Bros.' fourth-generation family business is still booming. They make their hats just as they were made 100 years ago—hand blocked on old wood forms and stitched in small factory workshops in New Jersey, Great Britain, and Italy. In addition to the classic Bowlers and Top Hats the company has been producing since the 1890's, they've come up with more modern styles like slouchy knit beanies and colorful wool cloches. With proper care, these are hats that will last generations.
Pick up a hat for a stroll in this iconic district and head on over to one of the many neighborhood bars to show it off—Comstock Saloon, Rogue Ales Public House, and Vesuvio Café are some neighborhood favorites.