Gap’s latest slogan is a mere three words, as simple and tactile as its new wide-legged denim: “Feels Like Gap.” At the 56-year-old clothing empire’s San Francisco headquarters, the words are emblazoned in all capital letters between the elevator banks at 2 Folsom St.

Feeling seems to be how Gap is finding its way back to its roots. The brand has been leaning on what it does best to imagine its future: Recently, you may have seen its crisp ad campaigns filled with infectious pop music and high-energy dance moves, association with generation-straddling icons like Parker Posey and recommitment to quality basics for a wide audience — tried-and-true methods the brand fine-tuned from a modest Ingleside shop selling vinyl and jeans.

‘Fall Into The Gap’

When the first Gap store flung open its doors on Ocean Avenue in 1969, it sold two things: records and Levi’s. The groovy outlet was the dreamchild of Doris and Don Fisher, the latter of whom was frustrated he couldn’t find jeans in his size.

Don might have provided the idea, but Doris provided the name (Don’s suggestion was “Pants and Disks”). She played off the idea of a generation gap, and the concept parlayed into smart marketing appealing to a broad audience — the young and hip and those wanting to seem young and hip.

Art Twain, who worked as a copywriter for Levi’s, as well as Gap, wrote in Don Fisher’s limited-release 2002 autobiography, “Falling Into the Gap: The Story of Donald Fisher and the Apparel Icon He Created,” that at first he didn’t like The Gap as a name. But soon he saw its potential as a short phrase that fit easily into marketing campaigns. “It was good fodder for advertising,” he wrote.

Gap’s initial, simple slogan doubled as a song: “Fall Into The Gap.” Music has always been core to Gap’s identity; concentric circles decorated that first storefront on Ocean Avenue to mirror the records spinning inside.

And Twain came up with one of the brand’s most successful print ads ever, according to Fisher’s autobiography, when he crafted a design for a 1970 store launch: “The Gap is open” the text read above a pair of jeans with the fly unzipped. The San Francisco Chronicle ended up pulling the ad because of reader complaints of it being pornographic, but the furor only ended up fueling the fun and loose image of the brand.

A year after opening in 1969, Gap had five stores within California. Five years after that, it had 186 stores across the country. “They were a force,” said Lynda Grose, professor of fashion design at California College of the Arts. “Something to be reckoned with.”

The company had moved on from selling only Levi’s to producing its own line of denim, as well as casual separates. The brand began with tops, since Levi’s didn’t have much selection in that category, producing woven shirts and knits. Gap Inc. went public in 1976 and began adding to its portfolio of brands: First came Banana Republic in 1983, then Old Navy in 1994, and finally Athleta in 2008.

Even if people might not have known Gap was born in Ingleside, the company became synonymous with the city. “San Francisco has a relaxed style, effortless but still stylish,” Grose said. “And that’s at the heart of Gap. It’s in its DNA.”

Gap’s zenith came under khaki wizard Mickey Drexler, who became the CEO of Gap Inc. in 1995 after serving as Gap’s division head. Credited with the rapid expansion of the brand and the transition from Levi’s boutique to casual separates powerhouse, Drexler left the company in 2002 and went on to helm J. Crew.

The company struggled under a rotation of CEOs — and it wasn’t clear if Gap would find its footing again.

Back to basics

According to retail analysts, the string of new leadership coming after the khaki king didn’t seem to have the vision to keep the brand relevant in an increasingly competitive market.

“Gap had appointed insiders, people who had worked for Gap for a number of years,” said Neil Saunders, managing director of GlobalData Retail, which analyzes trends and patterns across the retail industry. “I don’t think they saw the change that was needed at Gap.”

The brand had become the whipping child of popular culture, pilloried by “Saturday Night Live” in a series of savage sketches known as the Gap Girls and infamously mentioned by Ryan Gosling when he told Steve Carell to “be better than the Gap” in “Crazy, Stupid, Love.”

Add to that some disastrous collabs — like a high-profile trainwreck with Yeezy that the company severed in 2022 — and the brand seemed to lose its identity further, a trajectory that’s mirrored in the habits of Generation Z customers.

Mary McPheely works in the nonprofit sector and lives in San Francisco, but she grew up in New York, where her fashion designer mother would take her on regular shopping jaunts to the Gap. “It was my favorite place to shop as a kid,” she said. But she moved away from the brand as a teen, when she perceived the styles to become more mom-ish. “As Gen Z would describe it — cheugy,” she said. She shifted to thrifting instead, which felt more sustainable and fun. But Gap didn’t disappear.

“When I was thrifting, finding a vintage Gap piece was the most exciting thing,” she said, mainly because of the high quality and great, timeless style. As a rabid “Project Runway” fan, when McPheely heard about the addition of Posen to Gap’s creative team, she decided to give the brand a second look. “It was so noticeably different to me in terms of the silhouettes,” she said. “It was a lot more elevated but still very classic.”

Alex Cohen, a 23-year-old Apple employee who does styling on the side, didn’t grow up going to The Gap, but she has baby pictures of herself wearing the brand. She recently started borrowing Gap basics from her roommate and soon found herself putting together a cart online.

For both McPheely and Cohen, the boatneck long sleeves are their favorite pieces — basics they can layer their own self-expression onto.

“The ’90s nostalgia vibe is a big pull for me,” Cohen said. “The big sweatshirts, the mom jeans.” She thinks the prices are fair for the quality and is eyeing some linen pants for her next purchase. She also cited inspiration from “White Lotus” and Posey. “She’s kind of an icon,” Cohen said.

For Gap to find its way back to itself, it had to find its way back to being San Franciscan: casually stylish, and effortlessly so.

The rise (again) to prominence

And slowly but surely, it’s making its way back into the cultural zeitgeist. The company reported strong fourth-quarter earnings in March, with Gap brand up 7% in the fourth quarter of 2024. Celebrities can be spotted wearing Gap once again: Timothée Chalamet wore a black satin GapStudio ensemble to an Academy Awards nominee dinner, Anne Hathaway showed off a custom Gap shirtdress at a Bulgari event, and Demi Moore sported a Gap cropped denim moto jacket to the San Francisco International Film Festival — appearances that echo the days of Sharon Stone emerging on the red carpet in Gap. Even TikTok users are highlighting Gap’s appeals— the ’90s nostalgia, the quality wardrobe staples — giving the brand free advertising.

The reinvigoration comes in part from CEO Richard Dickson, who joined the company in 2023 after breathing new life into Mattel’s Barbie. “Before Richard came into the post of CEO, it was a very staid brand,” Saunders said. “It was pretty boring, and it wasn’t connecting with customers.”

Previous attempts to reinvigorate Gap hadn’t succeeded, Saunders said. But thanks to Dickson’s smart decisions—like hiring celebrity designer Zac Posen as creative director in 2024 — there’s a vibrancy at Gap Inc. that’s trickling down through all the brands.

“Over the past year, it has managed to put itself in place where it is growing,” Saunders said. “That is quite exceptional for Gap, because it really does reverse many years of decline.”

San Francisco comeback

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With its rowdy beginnings, queer past and parrot-filled hillscape views, there may be no corner that better embodies the spirit of old San Francisco than the rocky climbs of the city’s Italian district, North Beach. It’s also where Zac Posen lives, and where his favorite vintage store — Vacation — stands.

“He’s in here all the time,” said employee Megan Lortz. She likes the changes she’s heard about Gap corporate, including the partnership with Sean Wotherspoon, which she hopes could lead to Gap and Banana Republic stocking vintage sections in their stores one day.

Retail analyst Saunders believes the Posen hire was about something entirely different than designing clothes. “It was actually to elevate the thinking internally,” he said, as if Posen’s background in designing evening wear coupled with his effervescence could rub off on the company’s brands.

If Gap was flailing before because it was, in part, failing to tell a story, now it’s succeeding, in part, because it’s doing so once again. The fresh approach is reflected in the space of the stores, which hum with a new energy.

In the flagship Gap on Folsom Street, four-by-four-screen banks pulsate with dancers animating the new denim line, and pieces are displayed as looks, not individually. The Chestnut Street store has a single screen but the same tendency to display outfits instead of items.

Yet all of this progress does not mean that the work for the company is finished. “It’s not like they’ve had a year of growth now, so everything’s solved,” Saunders said.

Others agree. Mark A. Cohen, director of retail studies at Columbia University who worked alongside Gap founder Donald Fisher in the 1970s, invoked the title of Richard Fariña’s novel “Been Down So Long It Looks Like Up to Me” to describe his feelings about the company.

“It feels like the Gold Rush, in terms of some people make it, and some people don’t,” Grose said. “It’s reassuring they’re still around.”

The recent promo film for the collaboration with lauded London skate brand Palace, named Palace Gap, was shot entirely in San Francisco. It features sweeping views of cable cars, the Transamerica Pyramid, skate legends like Elissa Steamer and Tommy Guerrero at the Embarcadero, coffee at St. Francis Fountain, and the Golden Gate Bridge. It feels like a love letter to the city.

“We’re really committed to our hometown of San Francisco,” said Calvin Leung, head of creative at Gap brand. “It inspires a lot of our work, and we’ve had some great moments this past year to pay homage to our roots.”

Gap, at its heart, played a paradox — being fashionable without caring about it. Its separates were basic enough you could layer your own style on top of them, and they were quality enough to last to pass on to a new generation. That’s exactly what happened to one generation of San Franciscans, holding corduroy coats or five-pocket denim in their closets for themselves or a vintage store. That remained the best kind of Gap while it careened through an identity crisis — and it seemed like the city it was born in was, too.

Gap resuscitating itself after more than a decade-long slump seems to mirror the trajectory of the city in which it was born. Both, ultimately, shine glimmers of hope — and each is tightly interwoven into the fabric of the other.