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Like many other brands, including J. Crew and Ulla Johnson, Gap is curating its own vintage items for resale. Earlier this year designer Sean Wotherspoon went on the hunt for Gap finds from the 1980s, 1990s and 2000s. This month the brand released a new collection from him inspired by the Gap of those decades.

In other words, from when the brand defined American style.

It is no small thing to define or even, arguably, elevate American style the way Gap once did. Unlike Ralph Lauren, whose own influential definition evokes a sort of hip aristocracy from the American West, Gap is democratically, inclusively and diversely American, according to Thomai Serdari, director of the Fashion and Luxury MBA at New York University’s Stern School of Business. 

“Gap to me is what is good about being in the United States,” she said by video conference. “It's opportunity, the opportunity to be creative, to go to college, make friends, play soccer or basketball or whatever. All ethnicities, all races, every generation in the States look good in Gap merchandise. Gap doesn't quite break the rules, but Gap wants you to do it your own way — that's why the brand can adjust to every personality. And I'm sorry that I cannot see that any longer.”

How Gap gave basics character

Gap was founded in 1969 as a lone San Francisco store selling third-party brands. Five years later it transformed into a specialty retailer with its own merchandise. The brand still sells a lot of clothing, notching $3.8 billion in net sales last year.

That’s down from its peak of $7.3 billion 20 years ago, a decline that has been relentless.

“Gap has the rather difficult assignment of managing both an opening price point and middle market offering of ‘everyday apparel.’ No easy task,” Jeffrey Sward, founding partner at Merchandising Metrics, said by email. “I for one think it's really healthy to remain mindful of the ‘every generation’ aspect of Gap's heritage. You cannot underestimate the importance of marketing. Gap at its peak was all about mundane product with brilliant marketing. I will always find the ‘Swing’ campaign to be a great example of that, and that was long before what we have learned social media can bring to the table.”

“Khaki Swing” was an exuberant 1998 television ad featuring dancers in Gap khakis, tank tops, T-shirts and button-downs doing the Lindy Hop to Louis Prima’s 1956 hit “Jump, Jive, an’ Wail.” The spot took advantage of, and helped spur on, a momentary resurgence of swing. Prima’s wife and performance partner Keely Smith, who also sings on the tune, told the South Florida Sun Sentinel in 2002 that it reignited her career.

“That Gap commercial did wonders,” she told the paper.

By then, Gap was well established as a savvy marketer of its apparel basics. In the late 1980s, the brand produced a series of print ads titled “Individuals of Style,” which returned as an exhibit at the National Portrait Gallery in 2007.

 

Perhaps the brand’s most audacious campaigns enlisted cultural icons who weren’t even wearing its clothing, and in some cases had died before Gap was even founded.

Audrey Hepburn (or, more accurately, a clip from her 1957 movie “Funny Face”) had the job for a 2006 ad for Gap’s skinny black pant. Instead of dancing before a mortified Fred Astaire, Gap’s edit has her leaping into a mashup with AC/DC’s “Back in Black.” 

The epitome of selling clothing without featuring an actual stitch of it, though, came before, in Gap’s 1993 “Who Wore Khakis” ads. The marketing team dug into photo archives to find superstars from every realm — including Mohammed Ali, Salvador Dali, Miles Davis, James Dean, Amelia Earhart, Earnest Hemingway, Arthur Miller, Andy Warhol and John Wayne, among many others — wearing khakis plus other garments you might find at Gap stores.

At the turn of the century, Gap’s marketing still held wide cultural authority. Speaking on the “One Song” podcast this summer, writer-comedian-DJ Diallo Riddle noted the influence of Gap ads in the early aughts.

Riddle recalls discovering a neo-soul song of the era via a Gap ad, something that he said often happened back then. “But that was like when Gap commercials could break songs. Like I'll never forget the Gap commercial that had ‘Lovely Day’ by Bill Withers, and it had all those cool dancers on, and all of a sudden all DJs were getting requests for Bill Withers, all of a sudden. And it wasn't ‘Just the Two of Us.’ It was ‘Lovely Day,’ which is to this day one of his most lovely songs, you know. So that was when Gap was breaking songs, like TikTok.” 

A lack of creativity

As the 21st century progressed, however, Gap struggled to reflect an American ethos that all kinds of people could embrace, and would buy. Much of its growth derived from enlarging its store footprint, a massive expansion that the company has since walked back.

“I remember my neighborhood around NYU, and there were several Gaps, across from each other. That's pure insanity,” Serdari said. “So it was artificial growth. The analysts were happy with the evolution, but it wasn't a real and sustainable growth.”

Discounts were also emerging as a lure. In 1994, to compete with retailers like Target, off-pricers and fast-fashion stores, which were enticing customers with appealing designs at low prices, the company founded Old Navy. The brand took off, notching a billion dollars within four years. Old Navy steadily caught up to its higher-priced sibling, and by 2014 its trajectory was rocketing upwards as Gap plummeted. In 2017, the company announced that Old Navy would underpin its growth strategy.

Within the business, aside from competing with its own, lower-priced sibling, Gap lost the creativity that had led to such resonant merchandising and marketing, experts say. Some analysts peg the problem to the tenure of Art Peck, a former Boston Consulting Group executive and 15-year Gap Inc. veteran, who held the chief executive reins at the parent company from 2014 to 2019, which by then was also running Banana Republic (acquired in 1983) and activewear line Athleta (acquired in 2008).

Serdari believes that, even earlier, data began to supplant the Gap brand’s inventiveness.

“I think for them, it's all about losing that sort of creative spark, and shifting their focus into bringing in a load of data analytics, trying to predict the market based on big data,” she said. “Big data is very useful, but not with no creative person at the helm organizing everything. I don't know why there is such a huge split — only in the U.S., in Europe, that's not the case at all — where we cannot reconcile the analytical part of a company with the creative part. That's their problem, basically, with technology promising a revolution. You cannot deal with creative industries with that approach.”

Perhaps Gap realizes this on some level. Some point to its ill-fated partnership in 2020 with Kanye West, now known as Ye, as an attempt to return to artistry, or at least get some attention. Wells Fargo analysts predicted Yeezy Gap could be a billion-dollar brand, but its slow-moving drops, initially a series of puffer coats, disappointed many. The effort collapsed in 2022 as Ye displayed problematic behavior, including antisemtic and racist remarks.

“What happens is, you hire a Yeezy, who has absolutely no merchandising skills whatsoever,” Lee Peterson, executive vice president of thought leadership and marketing at WD Partners and previously a merchant at The Limited, said by phone. “That coat they put out was the worst thing I think I've ever seen. There wasn't even a zipper on it. And I'm like, that’s in the Gap?”

As of August — 54 years to the day when Gap launched — Gap Inc. has a new CEO, former Mattel executive Richard Dickson. Given the remarkable Barbie revival that happened under his watch, he’s under pressure to deliver a comeback. For any overhaul of Gap, he will be working with Mark Breitbard, who returned to the company in 2017 and has overseen the Gap brand since 2020.

Gap is not Barbie, however.

“Gap is incredibly boring and does very little to entice customers into buying its products – especially not at the high full prices it charges, hence why it so often resorts to discounting to shift stock,” GlobalData Managing Director Neil Saunders said by email. “The Gap brand has long been the problem child of the group, and its relevance in the market is one of the biggest issues new management will need to tackle if they want to turn around the fortunes of the company.”

The Gap x Sean Wotherspoon projects, which reach back decades, are running alongside a nostalgic marketing campaign that recognizes Gap’s former place in American culture. These may be signs that the company is beginning to appreciate what it took to offer something meaningful at Gap, according to Serdari. To recapture its soul, though, the brand must loosen its grip on data analytics, which only reflects what was, and get creative again, she said.

“They need someone who's very good with branding and merchandising and storytelling. They need different designs, too, because the designs right now, they have no character,” she said. “People still dress like that, though, in khakis and sweatshirts, so it's not irrelevant. It is not outdated. Why shouldn't you able to revive a brand that has that long heritage?”