Hip to Be Square

Inside Pia the Store

Photo Credit: Drew Altizer

On the border of the Financial District and North Beach, Jackson Square is one of San Francisco’s most beautiful and underrated neighborhoods. The area is full of rich history: During the Gold Rush, Jackson Square was part of what was known as the Barbary Coast—the waterline came all the way up to Battery Street—and it housed factories, saloons, and brothels that were frequented by the sailors who came into town. Today, it’s a relaxed and quiet neighborhood that’s home to luxe boutiques, architectural firms, antique shops, and iconic restaurants. It’s the preferred shopping place for many a San Francisco swan. According to local star stylist, Mary Gonsalves Kinney, “Jackson Square is a favorite shopping destination because it’s off-the-beaten Union Square path and offers a wide variety of hard-to-find, European designers. Those that open shop around that neighborhood seem to be slightly more art-focused and avant garde.” We couldn’t agree more with Kinney. Here we highlight our must-visit Jackson Square spots. And a word to the wise: there is no physical square in Jackson Square, but instead simply chic storefronts lining charming streets.

Pia’s storefront changes often

Photo Credit: Drew Altizer

Farnaz Dadashi, a local stylist who works at Pia the Store, describes Jackson Square as “the underground place for women in the know to shop.” Judging by the people who showed up for the airy boutique’s opening last fall, Dadashi is right. Owner Pia Cohler counts Priscilla Chan Zuckerberg, Nicole Systrom, and Alison Pincus as fans as well as plenty of cool girls about town like ballerina Maria Kochetkova, artist Anna-Alexia Basile, and event planner Rebecca Revel. Cohler hand picks each piece of clothing  and she tries to secure items that won’t be found elsewhere in San Francisco. With white walls, high ceilings, and light streaming in from large windows, Pia’s decor is minimal, but that allows the clothes to take center stage. The beautiful collection that Cohler has put together includes sexy chiffon dresses, one-of-a-kind statement coats, cozy sweaters, and sophisticated chic basics. Downstairs shoppers can find stylish separates and pretty dresses from Alberta Ferretti, Rachel Comey, and Zimmerman while upstairs is athletic, leisure, and denim from Paco Rabanne, Raquel Allegra, and Frame. “When I have a hankering for something with a bohemian French vibe, I can venture into Pia the Store,” Kinney says of this upscale seven-month old boutique, so if that’s the sort of thing you’re on hunt for, you know where to find it.   

Several doors down from Pia is Theory, the contemporary American fashion label’s newly opened, second stand-alone boutique in San Francisco. Theory is a luxe lifestyle fashion label designed by Lisa Kulson that specializes in timeless basics. Simple, but expertly cut blazers, chunky knits, slouchy track pants, silk dresses, and work shirts fill the racks at the bright and airy boutique. With white walls, light wooden floors, high ceilings, and exposed beams, the space reflects the minimalist chic look of Theory’s classic aesthetic. 

Womenswear by Jake

Photo Credit: Tony Sananikone

One of the things that makes Jackson Square special is its close proximity to the TransAmerica tower. Look up any which way, and the city’s most iconic skyscraper reaches up to the sky. If you happen to be on Sansome taking in the majestic beauty of the building, you may notice a colorful Rubik’s Cube mural. This means you’re around the corner from Jake, a decadent haute couture design house. Thanks to a stint on Project Runway, Jake Wall is one of San Francisco’s most well known original designers. With Jake, his namesake fashion brand, he brings to life polished dresses and impeccable suiting for stylish men and women who aren’t afraid to make a statement. Walk into the large boutique and it feels like you’ve been transported to a sumptuous European salon. There is white marble, tufted leather couches, and racks filled with Jake’s provocative and thoughtful creations. Although it’s decorated in cool colors, there is nothing cold about Jake. Wall’s two greyhounds greet shoppers with a gentle nuzzle and sketches of upcoming projects are taped to the mirrors giving it more of an artist’s studio vibe than overly pretentious showroom. Jake’s current collection, Les Liaisons Dangereuses, consists of quilted bomber jackets, bell-sleeve mini dresses, sleeveless kimono jackets, and a unique custom chinoiserie print made in collaboration with the Walt Disney Family Museum.

A guideboat on display at its namesake shop

Photo Credit: Roland Manuel For Guideboat Co.

If you’re not in need of a gown or tuxedo, but lack sporty supplies, there are several must-visit shops in Jackson Square. At Guideboat, you’ll find rugby shirts, leather-strap watches, military-inspired totes, and much more. The store is an all-encompassing selection of everything one needs to enjoy the great outdoors. Guideboat was launched by Stephen Gordon, the original founder of Restoration Hardware, as a retail boating business. A guideboat is a lightweight wooden row boat that was used in the 1800s to guide fishermen and hunters in the Adirondacks. Gordon’s vintage 1892 guideboat inspired him to launch the appearal and sporting goods brand, which also sells sleek, fast modern replicas. The California-made boats are solid American cherry with hand-laid hulls and a shiny midnight blue finish, waxed to perfection. These are the most gorgeous row boats you’ll ever see. They weigh only 89 lbs, so they are easy to transport from a car’s rooftop to a river. Other items Guideboat sells? All the goodies you need for a perfect day on the lake: sailing shells, seafarer boots,  pocket compasses, and aviator sunglasses. Plus, plenty of fun gifts like hurricane lanterns, pressurized growlers that will keep 128 ounces of beer cold for weeks, Estwing sportsman’s hatchet with laminated leather grip, and books like John Muir Wilderness Essays and the Morrow Guide to Knots.


Prefer biking to boating? Walk down Hotaling Street, a one-block alley, and you’ll come to Shinola, a Detroit-based bicycle manufacturer and leather goods producer. The year-old 3,200-square foot space offers a full lineup of quality goods, from leather backpacks to gold cuffs. Many of the items are customizable. Build your ideal watch by choosing the strap and time face, engrave a leather journal, monogram a wallet, or place your initials on a silver locket. The beautiful bikes have a nostalgic quality to them and come in a variety of styles and colors. We love the Runwell, an 11-speed bike inspired by the French Porteur bicycles once used by newspaper couriers on the streets of Paris. The store is housed in a landmarked building, the Belli, which was originally built during the Gold Rush—it has a lovely center courtyard patio that often is a hub for local maker collaborations. Since opening, Shinola has partnered with many brands from Jessica Silverman to Mr. Holmes Bakehouse to host special events and sales. Shinola shares the retail space with Filson, a Pacific Northwest retailer established in 1897.

The fly fishing shop inside Wingtip

Photo Credit: David Dines

Filson makes men’s and women’s outdoor gear, luggage, and bags. Think plaid shirts, ultralight jackets, hiking boots, Henley sweaters, and durable pants. They also sell gear like fishing vests, gun cases, handmade knives, soft-sided coolers, maritime sleeping hammocks, and utility aprons. The only thing Filson doesn’t offer is fishing poles, but no matter as the dapper outdoorsman can shop for them nearby at Wingtip.  A modern men’s emporium, Wingtip is a one-stop shop that sells anything today’s gentleman may need. Custom tailored clothing? They’ve got it. Brands like Eton, Alfred Dunhill, and St. James of London clothing? Check. Cigars? Cufflinks? Check, check. Fly fishing poles? Wingtip has them! In fact, Lost Coast Outfitters, its fly shop, is the only place to purchase angler supplies in the city. There is also a superb collection of over 850 spirits and 350 wines, a barbershop manned by master barber and tastemaker Joe Roberts, and a private club on the 10th floor.