Establishment neighborhood
Jay Jeffers—THE STORE
1035 Post St., Tenderloin
Housed in a Tenderloin warehouse originally built in 1910, Jay Jeffers' eponymous store was a long time coming. His design firm has been around since 1999, but it wasn't until 2012 that the long-awaited brick-and-mortar finally opened. The store is a stunning reflection of Jeffers' signature style; eye-catching and interesting without being flashy, and simultaneously comfortable and sophisticated. As for the merchandise, you'll find plenty of bespoke furniture from talented designers and craftsmen, many of whom Jeffers has limited-edition partnerships with. If you're not currently redecorating, there's a healthy selection of books and a few fashion items, plus plenty of throws, pillows, and bar accessories to take home.
Bourbon & Branch
501 Jones St., Tenderloin
While Bourbon & Branch isn't the first bar to play on the speakeasy theme, they expand the motif with a lot of enthusiasm. Located in a bar that was an actual speakeasy from 1921-1933, the space has more than five secret rooms for guests to explore, if they can find them (and remember the password). Plus, a set of "House Rules" prevents anyone from using cell phones or taking photographs, and awesomely cautions: "Don't even think about asking for a Cosmo." Make a reservation in advance, as you'll need to be armed with a password to get in.
Redwood Room
495 Geary St., Tenderloin
This historic bar inside the Clift Royal Sonesta Hotel has been open since the '30s, when waiters in white tuxedoes served the drinks (indeed, the Redwood Room's conservative dress code made it an important battleground for clashes between San Francisco's old guard and the long-haired kids of the '60s). The art-deco style space underwent a complete restoration in the early 2000s, bringing the redwood paneling on the walls and the deep bar, which was rumored to have been built from just one redwood tree, back to their former glory. The vibe here can get a little clubby at night, so we like to stop by in the early evening for pre-dinner drinks.
Liholiho Yacht Club
871 Sutter St., Tenderloin
The Tenderloin is kind of having a moment right now with trendy spots popping up on the regular. With its huge open kitchen, slick bar, and generally awesome vibe, Liholiho fits the bill, but it also has the seriously good food to back it up. Think fancy-ish Hawaiian food—marinated squid, Spam fried rice, fried oysters—and killer drinks. For dessert, we've heard good things about the Baked Hawaii—like a Baked Alaska but…you know, Hawaiian. Big parties should spring for the family-style Ohana Table option.