Inside Gap’s Last-Ditch, Tariff-Addled Turnaround Push

When you’re inside the Gap Inc. headquarters, the grand promise of California stretches out to the horizon in every direction. The building is situated on an almost unfathomably valuable patch of real estate near the foot of the San Francisco-Oakland Bay Bridge where, between the building and the bridge, a giant bow and arrow sculpted by Claes Oldenburg and Coosje van Bruggen plunges down into the shore, as though an unseen Goliath is taking aim at China through the center of the Earth. It was commissioned more than two decades ago by Gap’s founders, Doris and Donald Fisher—part public art, part de facto insurance policy for their company’s panoramic view of the bay.

On the afternoon of April 2, as American retailers fretted privately over the tariff plan that President Donald Trump was due to unveil on a big, beautiful piece of foam board, this is the view that framed Richard Dickson in one of the company’s conference rooms. Dickson is the company’s fifth chief executive officer since retail legend Millard “Mickey” Drexler’s ouster in 2002 — which precipitated a more than 50 percent revenue decline, from a mighty $7.3 billion, for its namesake brand since 2003. He’s also the only Gap CEO who, at this point in his tenure, cannot be accurately described as “embattled.” At a company that’s been promising a return to glory for both shoppers and shareholders since the George W. Bush administration, the early results suggest a turnaround might finally be in the offing — as long as Gap can get its clothes right, wean the public off constant discounting, figure out what mall shoppers want from its stores and claw its way back toward the top of culture. No problem, right?

It was in this moment of optimism that Dickson was waiting for a trade war’s opening salvo to land. “We have 5 percent market share [in the American clothing market]. There’s plenty of business to go out and get. Even in a declining market, even when people say, ‘Well, how’s the consumer, the sentiment, the challenges?’ ” says Dickson, slender and tall and with a wardrobe full of studiedly unfussy Banana Republic sweaters and jeans. “This year it’s tariffs, next year it’s something else” — his voice rising in a nasal faux panic — “the Red Sea, the Blue Sea. It’s constant.”

That, of course, is what any CEO worth his compensation package is supposed to say in the minutes before a disaster of indeterminate magnitude is set to strike his industry. But in the moment, in the kind of setting that forces you to remember Gap can still marshal the resources of a Great American Company — not just the view, but the walls lined with black-and-white ads showing some of the coolest people to ever live, wearing clothes that decades ago changed global fashion — it seems almost reasonable.

By the time we exited the conference room, though, the tariffs were real. Real and bizarre — haphazard, onerous, seemingly designed to collapse as many US consumer businesses as possible. Dickson, he tells us several weeks later, had immediately gotten on the phone with the company’s chief financial officer and its chief supply chain and transformation officer to start working through potential scenarios for dealing with a much different set of duties than the industry had anticipated. “What if we increase production in the US? Why not?” he asked, enumerating some of the possibilities on the table. “What if we diversified our footprint even more? What if I went to the administration?”

Dickson and Gap’s government affairs team traveled to Washington several times to do just that. They talked tariffs, both directly with Trump and with congressional leaders, and discussed the potential for store closures. “The intent is good, but the reality of that — of executing in our category — is limited,” he says, referring to the quixotic task of bringing the garment and textile industries back to North America in any meaningful way.

This type of tariff torment is hardly unique to Gap. Any company that sells physical goods has been forced to take a frantic look at its manufacturing, sourcing and logistics operations and try to triage. In Gap’s case that means hedging the retailer’s import and product bets, and in its May earnings call, Dickson said the company aimed to diversify its overseas suppliers and ensure that no one country accounts for more than a quarter of its goods by the end of 2026. (In fiscal 2024, Vietnam was the only country above that threshold, at about 27 percent.) By the end of this year, Dickson said, imports from China, which as of 2024 accounted for less than 10 percent of Gap’s assortment, will be reduced to less than 3 percent. And the company planned to double its sourcing of American-grown cotton in 2026. “This is one of those moments that is going to require more patience,” which Dickson admits he doesn’t always have. Gap has been getting more traction with shoppers of late, he says, but “this is a factor that potentially will, you know, impact certain parts of our momentum.”

During the same earnings call, investors got a first look at what that impact might be. The retailer shared that it was expecting as much as $300 million in additional costs in the 2025 fiscal year, though planned mitigation efforts should reduce that by up to $150 million. The remark sent the company’s stock into free fall, ultimately down about 20 percent by the time the market opened the following day. Other retailers have issued similar warnings: After pulling its guidance for the fiscal year earlier in May, American Eagle Outfitters Inc., which has about a third of the annual revenue of Gap, said it expected around $40 million in tariff-related costs. Abercrombie & Fitch Co. — similar in size to AEO — predicted a $50 million hit.

US clothing retailers have been in a state of decline for decades. Like plenty of others from its 1990s heyday, Gap’s rise — and long humbling — largely mirror the ascent and demise of the mid-tier suburban mall. As foot traffic was disappearing in the mid-2000s, the brand got battered from all sides: European fast-fashion companies such as H&M; Target cementing itself as a force in affordable fashion; and Uniqlo’s Japanese basics. But many of Gap’s problems have been a self-inflicted jumble of nonsensical resource-drains, bad investments and failed concepts. Piperlime, its attempted Zappos.com competitor, shut down in 2015. In 2012, Gap tried to get into the high-end apparel market by buying the boutique chain Intermix, which went nowhere; Gap offloaded it to a private equity firm in 2021. Then there was the Great Yeezy Debacle of 2022, in which a planned decade-long collaboration with the rapper formerly known as Kanye West collapsed in a humiliating heap of $90 hoodies.

Through all these corporate side quests (and, quite frankly, too many others to list), what suffered was the thing people actually wanted from Gap: the clothes. While the retailer was looking to join new markets or close underperforming stores or bulk up its e-commerce operations, it seemed to forget that its core competency is, or was, designing cool, affordable everyday apparel. In the past year or so, the necessary cleanup of the company’s finances and logistics operations seems to have finally paid off, just as the chain’s clothes are starting to attract the attention of both teens on TikTok and the elder millennials nostalgic for Gap’s golden age — and who can actually afford $80 jeans at full price.

If you squint, you can sort of see how a company like Gap might be well positioned to weather, and perhaps even benefit from, the kind of direct hit to the industry that the Trump administration has so far outlined. Closing the de minimis exemption, which waived tariffs on imports valued at $800 or less, has given US clothing retailers some relief from the lowest-priced competition with Temu and Shein. Amazon.com Inc., which relies on third-party sellers, a significant portion of whom are overseas, could suffer. Smaller, less resource-rich American businesses are at a real risk of getting gutted too.

Meanwhile, Gap orders inventory at a scale that encourages its existing production partners, some of which the company says it’s worked with for more than 30 years, to prioritize its needs. And if it wants to find new production capacity elsewhere, in countries with less of a tariff target on their back, it can box out most of its competition. It may be a business that’s endured decades of missteps, failures and contraction, but it’s still bigger than the vast majority of companies selling similar products to US consumers right now. Dickson just needs to make sure, while steering all this, that he can also capture the more intangible thing that’s just as vital. “We’ve been around for 55 years,” he says, “and we want to be around 55 more.”

That Gap still exists at all is itself a minor miracle. Brands don’t have limitless lifespans, especially in an industry as fickle as fashion, and Gap’s obituary has almost been written many times over the past decade. Americans’ nostalgia for mall retailers hasn’t helped many of them survive, most having faded into either obscurity or, more likely, bankruptcy court.

The first Gap store was opened by the Fishers in the countercultural hotbed of 1969 San Francisco, selling Levi’s and records to the city’s cool kids. In the following years they opened dozens of stores and began developing their own low-cost clothing lines. They took the company public in 1976 and eventually jettisoned the third-party products in favour of their own. The next 25 years were stunningly successful as a casualising country turned to new suburban shopping malls — which sprang up as quickly as developers could get the stucco to set — in search of jeans, khakis and T-shirts.

That was thanks in large part to Drexler, whom the Fishers hired in 1983, the same year the company bought a safari-themed retailer named Banana Republic. Among other consequential decisions, Drexler cleared out the previous decade’s private-label experiments. Inside Gap there would be only one brand: informal but crisp, easy but traditional, preppy but not too preppy — the quintessential basics of American dressing. The clothes threaded a very tricky needle, satisfying mall shoppers while being cool enough for the fashion and entertainment elite. In 1992 a gaggle of supermodels covered Vogue’s 100th anniversary issue swathed in the company’s white jeans and button-downs; Sharon Stone wore Gap pieces on the Oscars red carpet twice. Meanwhile, Gap’s ads became art in their own right: black-and-white photos by Herb Ritts, Annie Leibovitz and Patrick Demarchelier, featuring cultural icons such as Spike Lee and Joan Didion; historical shots of Amelia Earhart and Muhammad Ali, cleverly repurposed to sell khakis; TV commercials that felt more like music videos. A 1998 profile in Fortune magazine speculated that Drexler just might be the most influential person in American fashion.

Inside the company, though, pressure was mounting from lower-priced competition aping the Gap model, and a bloated fleet of aging stores was beginning to feel less hip. Drexler found some fixes — most notably, launching the less expensive Old Navy, which buffered the company from more aggressive discounters. Gap (the brand) might have lost those sales, but Gap Inc. (the company) kept the market share. The strategy has been effective beyond what anyone could have predicted: It took only a few years after its debut for Old Navy to reach $1 billion in annual sales, and in the brand’s most recent fiscal year it brought in $8.4 billion, compared with the Gap brand’s $3.3 billion. Even so, by 2002 investors had grown restless and wanted new leadership. The company’s financials were messy and debt-laden, and sales had been declining for two years; Drexler was fired. The next year, Gap posted what are still its best sales numbers by selling the clothes that Drexler, by then CEO of J.Crew, had ordered into production before being shown the door. (Drexler declined to comment.)

The less that’s said about what’s transpired since, the better. “Gap’s had just a string of different leaders — like, a revolving door of leadership,” says Mark Breitbard, who joined the company for the first time in 1997 and in 2020 was named president and CEO of the Gap brand. (This is where we acknowledge, not for the last time, that it’s a little confusing that the company shares a name with one of its brands.) Breitbard isn’t quite a Gap lifer, but close, over the years tasked with some cleanup at three of the company’s four brands. (The outlier is Athleta, the activewear line it acquired in 2008.) In other words, he’s seen some things. “Gap had more fundamentals to fix,” he says. “Broken international markets, stores that were unprofitable, SKU proliferation, lack of focus, lack of big ideas.”

Every time the company hired a CEO, it was with the promise each would solve a diagnosed problem — to bulk up the e-commerce operation, to close stores, to get out of bad mall leases, to improve margins. After Drexler came Paul Pressler, previously a Walt Disney Co. theme park exec, who oversaw cost cuts and declining creativity. Next was Glenn Murphy, who’d previously run a Canadian drugstore chain; he too was heralded as a cost-cutter, and he implemented store closures and, ultimately, declines in product quality. The Murphy era had a few bright spots, such as a successful bet on colorful jeans in the early 2010s. He retired in 2015. Next: Art Peck, a former management consultant who, among other things, had been running Gap’s digital division. He lasted until 2019, during which time he closed hundreds of stores and made the company even more reliant on discounting. In early March 2020 came the unfortunately timed arrival of Sonia Syngal, previously the head of Old Navy, whose tenure was immediately thrown into chaos by the pandemic; she left in mid-2022. (Pressler defends his tenure, emphasising he accomplished what the board asked him to. Murphy, Peck and Syngal didn’t respond to requests for comment.)

Dickson’s first encounter with Gap began when he was still fully enmeshed in “Barbie”-mania, unleashing 100 brand deals or collaborations connected to the movie. After he’d worked a total of nearly two decades at Mattel Inc., he was contacted to consider joining the Gap board. He was intrigued by the high stakes. “I haven’t been to a Gap in a really long time, and when I looked at it online, I was like, ‘It’s lost the narrative.’ And then of course when I looked at the business, it was really not good,” says Dickson. “For me that was the draw. ‘Pick me, pick me, I’ll jump in the fire.’ ” He joined the board in 2022, just as the Yeezy collab imploded. By the following year, Gap was still looking for a CEO to replace Syngal, and with the “Barbie” movie about to premiere, Dickson decided he was up for the rehab job. Even though he was a toy executive, the board was impressed with his combination of creativity and financial discipline, according to a person familiar with the process who asked not to be named because the matter was confidential.

Yet Dickson was hardly a stranger to apparel. He grew up in New York City with parents who both were in the fashion business; at one point his father served as the CFO at Calvin Klein. His first job after college was at Bloomingdale’s, where he brokered a deal with a group of the city’s private schools to design a line of uniforms for students. He went on to co-found and then sell a dot-com-era online cosmetics retailer and become an executive at the apparel company Jones Group — always with an eye toward branding.

One of Dickson’s first acts as Gap CEO was to take his new leadership team on a shopping trip — to Gap.com. He wanted them to see with fresh eyes what bugged him about the experience: how discounting schemes, sometimes several overlapping at once, had usurped the clothes as the brand’s focal point, which had been a problem for years. With the exception of that 2010s big bet on brightly colored skinny jeans, it was hard to recall a single moment in the past couple of decades when Gap’s clothes got people excited. Instead the retailer relied on deep, constant discounts to keep mediocre clothes moving. “You were like, ‘I don’t even see the product anymore, because you’re bombarding me with what looks like anxiety,’ ” Dickson says.

As the company’s new leader, he also noticed something askew among his staffers: an unrealistic culture of positivity. “I sit in meetings, and they’re all telling me how great things are, and they’re not — like, they’re just not great. So I’m fascinated at this culture that presents with such great positivity and optimism, but then you look at the business, you go to our stores, you go online, you hear the drumbeat in the outside world, and they think very differently,” says Dickson. At a town hall he presented all the negative headlines from the brand’s recent press. “I said, ‘It’s unbelievable. Everybody seems to know what to do but us. And you read the articles, and they’re not wrong.’ ” He wanted an environment where people felt compelled to identify failures, be honest about them and move forward. “I’m very transparent to the extent that it can be somewhat uncomfortable,” he says.

Externally the biggest boost to the company’s image in Dickson’s earliest days came from a splashy hire: the February 2024 appointment of designer Zac Posen. Posen, who rose to fame in the 2010s on the strength of his red-carpet gowns and his charm on “Project Runway,” is now executive vice president and creative director for Gap, as well as chief creative officer at Old Navy. He joined a company that had brought in flashy creative heads — one poached from a French fashion house, another with minimalist Scandinavian cred — only to then fire them or eliminate their roles entirely.

So far, Posen’s creative director title at Gap has caused confusion, the press crediting him for elements of both the company’s and the Gap brand’s overall performance—even though he doesn’t have much to do with the latter. His official corporate bio vaguely describes him as “a cultural curator and creative partner” to Dickson, in addition to the more straightforward design and product oversight duties you’d expect from Old Navy’s CCO. Posen’s most obvious public role has been in celebrity relations, creating custom Gap-branded looks for A-listers, including a red-carpet getup for Demi Moore and a Met Gala look for Da’Vine Joy Randolph. Asked about Posen’s role, Dickson says he’s “bringing more designers into the company through his recruiting skill set, bringing more interesting people into the cultural conversation based on who [he] knows and how [he] navigates in the culture.” He also says Posen’s role has been a boon to Gap’s marketing efforts. (Posen wasn’t made available to Bloomberg Businessweek for an interview, but we did see him at the company’s Tribeca offices dressed like an old-timey aviator. He smiled and waved as he passed our conference room.)

At Old Navy, Posen has overseen the release of a hit occasion-wear collection — inexpensive party dresses and taffeta skirts with matching crop tops for when you don’t want to spend $250 to attend a wedding — the development of which was already in progress when he joined the company. Where his aesthetic influence is most visible, though, is at GapStudio, a separate new line with a more fashion-forward sensibility and slightly higher prices, where Posen has a design staff of his own. Its one collection so far features things such as corset belts and nipped-waist trench dresses, as well as a reproduction of a virally popular off-the-shoulder shirt dress he created for Anne Hathaway to wear to a 2024 Bulgari event in Rome. The collection received an uneven reception from critics and shoppers. “The clothes, however, are … not right,” wrote Lauren Sherman of the first GapStudio collection in Line Sheet, her Puck newsletter on the fashion industry. “Nobody wants a denim trench, or a too-purple navy blue bubble skirt (even if it’s cute) from the Gap. You know what they want? A T-shirt. Fetishize the T-shirt.”

Barrel jeans, with their exaggerated curved legs that resemble a bowlegged cartoon cowboy, are the opposite of an obvious crowd-pleaser. If you walk into a Gap store now, the preponderance of barrel jeans — along with their even more exaggerated sister look, the horseshoe jean — styled with everything from tiny tank tops to oversize Oxfords should be your first hint that things are a little bit different at the brand. About a year ago, Gap finally rushed into a trend at the exact right moment for its shoppers. “We had a barrel fit two years earlier that we tested, and it didn’t test well because we were too early,” says Gap president Breitbard. “It worked OK in Japan, but it didn’t work in the US.”

For years, Gap has had an uneasy relationship with fashion trends, either betting big on things that didn’t end up catching on and then heavily discounting them, or not being able to get of-the-moment designs into stores quickly enough to capitalize on spiking interest. But with these jeans, Gap finally managed to capture a little bit of the magic it had at its peak, translating an edgy look into something approachable for a much wider swath of Americans. “We kept playing with it, and when the trend was there, we were ready to go,” Breitbard says. There was also an unexpected upside: Turns out when you wear jeans that balloon out, you need to offset them with some snug new tops, which boosted the average order size when customers purchased baggy jeans.

When Dickson arrived, some of the company’s hard rehab work was well underway. “Richard comes in, and a lot of the heavy lift — that’s the ugly part — had been done,” says Breitbard, adding that “all the flames were embers ready for gas to be poured on them. I feel that that’s Richard’s strength—coming in and taking these ideas and just making things much bigger and more explosive.” For years one of legacy retailers’ biggest challenges was their reliance on the old-school fashion calendar, which required them to design and order products six months to a year in advance, leaving them flat-footed in the face of fast-fashion companies that could pounce on trends. Breitbard changed that: Now, rather than being locked into designs, the brand chooses textiles early in the product development process, then waits as long as possible to decide which styles they’ll be made into. Along with this newfound flexibility and speed, the company can also test smaller batches of products with real customers before committing to larger orders. “Right now it does feel like we’re bringing back that aesthetic intelligence, that voice of taste,” says Calvin Leung, the brand’s head of creative.

Of course, telegraphing taste requires more than product. In 2023, Gap cast Veneda Carter for the kind of photo shoot that’s long been a signature — a spare portrait against a grey background. Dressed in baggy men’s jeans, a grey hoodie layered over an oversize button-down, and a logo trucker hat, she looked the part of the too-cool Gap icon. But unlike her ’90s predecessors, Carter isn’t mainstream famous; she’s a stylist and jewellery designer, mostly unknown to the public, but whose fashion-world cred sent a sharp signal to tastemakers who can get a “Gap is back” rumor going among their friends and followers. “We were getting a lot of interesting questions from the right people about, like, ‘Wait, what’s happening?’ And that was before there was any big story,” Breitbard says.

That growing buzz has also been aided by recent collabs with smaller, culty brands. In the past few years that’s included the zoomer-beloved sweatshirt brand Madhappy, the glam-hippie women’s label Cult Gaia, and Dôen, a Los Angeles-based label known for its feminine details and romantic sundresses. Gap reached out to Dôen in 2023 before Dickson was elevated to the top spot, according to Dôen CEO Margaret Kleveland, who along with her co-founder (and sister) had formed their understanding of casual American fashion in Gap’s heyday. “We all were already following the Instagram Gap playlist accounts and obsessed with old Gap creative and campaigns and portraiture as part of our visual points of reference,” she says, referring to popular social media accounts run by fans who compile digital odes to the Gap of yore.

If anyone at Dôen had questioned Gap’s reach after decades of shrinking sales, the collaboration’s first release, in May 2024, ended those doubts. Many of the products, including a $158 eyelet-embellished midi cotton dress, sold out in the first few days. Meanwhile the LA brand had its biggest day of web traffic ever, even though the co-branded products were available only through Gap’s sales channels. When the two brands paired up for a second drop this past May, Dôen enjoyed its best-ever sales week.

And for Gap? “You’re driving traffic and relevance, but you’re now driving new consumers to be interested in your basic core proposition that probably weren’t there before,” says Dickson. Kleveland says the biggest change she’s seen from the partnership is from women her age: mothers of young kids who’d mostly seen Gap as a place to get adorable clothes for babies and toddlers and might not have bought anything for themselves there since college. Indeed, on Mother’s Day a young mom pushing an infant in a stroller on the sidewalk of a leafy Brooklyn neighborhood was spotted wearing both the Gap x Dôen gingham shift dress and the matching chore jacket. Breitbard says that three years ago it was mostly Gap’s executive team reaching out for collaborations. Now, he says, brands are largely coming to Gap first.

But a multibillion-dollar chain can’t exist on collabs alone. Casey Lewis, a trend analyst and author of the After School newsletter, which dissects Generation-Z consumer behavior, says the clothes she’s seen get the most traction among young shoppers is stuff they’re discovering—and not necessarily from what Gap is advertising most widely. She mentions one Fair Isle‑ish cardigan that made the rounds online last winter. “It was not something that you would see in any of the Gap imagery, but it went super viral and sold out,” she says. “Young people are finding these items, and they’re digging for them and then posting about it.” A few days after we spoke, Lewis had a quasi-viral Gap moment of her own. She made a TikTok video about a linen-blend skort embroidered with little summer objects — a beach umbrella, a seashell, a pair of green fish. The clip now has more than 300,000 views, and the skort sold out (and was eventually restocked).

In February, New York magazine’s popular shopping-recommendation site the Strategist declared a “Gapaissance.” Leandra Medine Cohen, a longtime fashion influencer, sent out an edition of her newsletter proclaiming that “Gap is where it’s at.” The brand’s buzzy commercial with “White Lotus” star Parker Posey prompted a round of press, and Posen dressed Timothée Chalamet, the internet’s favourite celebrity, in a custom GapStudio look for the Academy Awards nominees dinner. Turning around a company with a half-century-plus of history, tens of thousands of employees and more than $15 billion in annual revenue is by no means a straightforward proposition, but if you were going to try it, this is probably what you’d hope it looked like.

Then, just a few weeks later, the tariff bomb went off. It brought with it a retail environment far shakier and more uncertain than when Dickson took the job. No one knows what the ever-changing tariff regime will ultimately look like (or, indeed, whether it will ever actually cease changing), which can make planning to mitigate the extra costs financially risky. After that disastrous May earnings call in which the company outlined how it planned to absorb some of the shock, Dickson held a town hall. He didn’t seem fazed by the $2 billion drop in market cap, instead reassuring staff that the company had exceeded financial expectations, according to an employee who attended and asked not to be named because they weren’t authorised to speak on the matter. Wall Street may have wanted even more growth, Dickson said, but everything was going according to plan—this was just some short-term pain.

The company has plenty of work to do within its own walls—in some cases, literally. Most Gap stores still seem trapped in amber from at least a decade ago, with crowded racks and piles of clothing amid bright white lights and washes of blond wood veneer. The Flatiron store in New York City is a little more modern, with gleaming white lacquer displays and clothes that aren’t quite as clearly separated by gender as they’ve been in the past. The Flatiron space is also trialing features such as a denim bar. But so far the company hasn’t committed to any particular improvements to its store fleet, and the ones it is testing aren’t incredibly inventive. Cautious incrementalism at an uncertain financial moment for retailers may be justifiable, but it may also turn off the Gap-curious at a crucial moment in the company’s revival—especially at still-bustling high-end malls where new store designs beckon shoppers from every direction.

A Steady Ascent for the Flagship Brand

Then there are Gap’s other brands. Old Navy continues to be the company’s workhorse, over the years having funded any number of boondoggles and misfires at its sister brands. “The revenues Old Navy does put it into a class of its own, along with Nike,” says Simeon Siegel, a managing director and retail analyst at BMO Capital Markets. At Banana Republic, revenue has declined by more than a third from its 2014 peak of about $3 billion. Weeks after Dickson arrived in 2023, the brand launched a line of furniture and home decor, BR Home, which he shut down the following fall. “It had a lot of flaws behind the scenes, and part of that flaw was the recognition that we had an apparel business that wasn’t healthy,” he says. Dickson has been running Banana Republic for more than a year following the departure of its CEO, who was hired for her expertise in home goods.

Athleta, the company’s smallest brand and a once-high-growth corporate darling, has also stalled out. Part of the issue is that Athleta’s premium prices force it to compete directly with trendier athleisure upstarts such as Alo Yoga and category leaders like Lululemon Athletica Inc. But some of the competition is coming from in-house. Old Navy’s own low-price line of gym clothes has quietly been beating its corporate sister brand at its own game with products designed to satisfy similar aesthetic and performance needs. Rumors have abounded that Gap might ultimately offload Athleta, though the company says it has no plans to sell the brand at this time.

At the Gap brand, executives have seen turnaround signs they like: sales growth from younger shoppers, the return of customers who’d strayed and people buying things without a discount. Of course, an undeniable element of its current good fortune is the trend cycle — looser, baggier jeans have lifted the performance, at least temporarily, of a number of brands associated with earlier eras of denim, including both Gap and Levi’s. Other trends — oversize button-downs, linen, hoodies — have also bolstered interest in the kinds of clothes that have always been quintessentially Gap. Peak nostalgia hasn’t exactly hurt either. Gen-Z has an obsession with clothes from the late ’90s and early 2000s, which has helped fuel comebacks at a handful of Gap’s contemporaries, including Abercrombie and Coach. To capitalize on the moment, Gap has enlisted the designer and streetwear collector Sean Wotherspoon to curate limited releases of the brand’s decades-old designs, which have so far all sold out.

If after all these years the Gap brand can finally execute a comeback, it could be well positioned for a tariffed apparel landscape. If prices go up and consumers are forced to buy less — or, perhaps, if some ultracheap products disappear from the country’s market entirely — some shoppers will look for better-quality options and more versatile pieces. Gap has already started signalling to polyester-weary customers that its clothes are often an upgrade, noting in product names when its sweaters are 100 percent cotton, a linen blend or cashmere.

In some ways, though, that means the pressure to pull this off is all the more acute. If Gap, with its decades of iconography and near-boundless goodwill among shoppers, can’t get it together this time, when the country is already demanding jeans and button-downs and hoodies, then what’s any of this for? In that way the greatest product of Dickson’s tenure so far isn’t a pair of jeans or a collab. It’s the ever-more-widespread belief that maybe Gap isn’t dead after all.

By Amanda Mull and Lily Meier