Richard Dickson hit the pink carpet at the London Barbie premiere last July wearing a blush-toned suit and magenta pocket square. He smiled for cameras with producer-star Margot Robbie and writer-director Greta Gerwig as fans—some of whom had been lined up in Leicester Square since 3 a.m.—looked on.
The event was a capstone of sorts for Dickson, who as Mattel’s then president and COO had helped transform Barbie from an outmoded feminist lightning rod into an icon of diversity, acceptance, and empowerment that attracted collaborations with the likes of Karl Lagerfeld and Balmain and sold $150 million in toys and consumer products last year. Now, here was the movie, which Dickson helped develop and executive produce. It would become the highest-grossing film of 2023.
But as the rosé flowed that night, few were aware that Dickson had already accepted an offer to become the CEO of the Gap. When news broke two weeks later, Dickson says, “People were like, the Gap? You’re making movies! You’re Barbie! It’s pretty messy at the Gap.”
That might have been an understatement. Gap Inc.—which comprises the brands Gap, Banana Republic, Athleta, and Old Navy—had announced just three months earlier that it was laying off 1,800 employees. Over a three-year period, 350 Gap and Banana Republic stores had closed. Even Old Navy, long the one bright spot in the portfolio, had become an earnings disappointment. For many consumers, the Gap had become a place to buy kids’ school uniform pants and the occasional deeply discounted sweater.
Dickson is now in charge of restoring relevance to a company that was once the preeminent purveyor of denim and khaki basics. In the 1980s and ’90s, the Gap helped enable mainstream cultural shifts like casual Friday, while attracting an array of edgy artists (Lenny Kravitz, Madonna) to make the idea of wardrobe staples feel exciting. Even when it wasn’t trying, Gap made headlines—Sharon Stone wore a Gap T-shirt to the Oscars in 1996. But the impact of fast-fashion brands such as Zara and H&M in the early aughts and the shift from malls to online shopping sent the company reeling.
Then came the pandemic, along with embarrassing misfires like the Gap’s collaboration with Kanye West. Today, as upstarts like Shein and Temu are appealing to Gen Z shoppers with TikTok-centered tactics and suspiciously cut-rate prices, sales at Gap’s brands have been shrinking. Global sales of the company’s namesake brand dropped to $3.3 billion in 2023 from $7.3 billion in 2003. Meanwhile, Gap’s $15 billion in annual revenue, while sizable, has remained virtually unchanged since 2001. “That’s not a growth story,” says Forrester analyst Sucharita Kodali.
Thankfully for the Gap, Dickson, 55, has experience with lost brands. When he arrived at Mattel in 2000, Barbie dolls had long gone out of fashion. Yet this challenge is different. Gap Inc. is a much bigger company. (Mattel’s annual revenue was just under $5.5 billion in 2023.) And unlike Barbie, a brand that many consumers had actively disdained, the collective attitude toward the Gap is meh. “People just don’t care,” said Marcus Collins, author of For the Culture: The Power Behind What We Buy, What We Do, and Who We Want to Be. “The ambivalence that people have about the brand [means that] you have to not only rework meaning, but you have to give people a reason to care to even allocate the cognitive energy to rework meaning. And that’s going to take some time.”
Dickson may not have much, given how quickly the Gap board has sounded the buzzer on its former CEOs (Sonia Syngal, who stepped down in 2022, lasted just two years). But there’s a reason that Wall Street sent company shares up 10% in the month after he was named CEO.
Dickson brings an outsider’s perspective, yet he has been on the Gap’s board since November 2022. He has won over fashion observers and the media with his candor about the Gap’s challenges, unusual for executives at the company, while being embraced by the Fisher family, which owns a 40.5% stake. (Board member Bob Fisher, son of founders Don and Doris, likes the way Dickson talks “about how the Barbie movie relates to people today. Clothes and entertainment are similar.”)
And then there’s Dickson’s chutzpah—a willingness to tackle hard jobs. “I’m drawn to the pain,” he says, cheerily. “I love the pain!”
It’s 4 p.m. on a Friday afternoon in April, and Dickson is sitting in a conference room at the Gap’s San Francisco headquarters, a view of the Bay Bridge occupying the floor-to-ceiling window behind him. He’s wearing a brown suede jacket from Banana Republic, a white Gap T-shirt, and colorfully striped Old Navy socks. Dickson loves clothes, something that Gap-watchers have noted with approval. “If you’re a fashion firm, you should have someone who’s interested in fashion” as CEO, said Neil Saunders, managing director of GlobalData Retail, a retail research agency and consulting firm. “You don’t want a bean counter in charge.”
Writer-director J.J. Abrams, who was tapped by Mattel and Warner Bros. to produce a Hot Wheels movie and who has collaborated with Dickson on toys, calls him “that rare executive who speaks creative. He has a real love of having actual fun and having an emotional, visceral reaction to something as opposed to data and algorithms and following the template of something that already exists.”
Dickson connected emotionally with the Gap in the same way he did with Barbie: by revisiting its origin story. Years before the Barbie movie was written, Dickson had begun reexamining Ruth Handler’s reasons for creating the doll in the first place—to unleash creativity and agency in little girls, instead of merely fostering maternal skills.
With the Gap brand, he’s zeroing in on the company’s original, radical mission to be a place where customers could buy jeans of virtually any size, following Don Fisher’s struggle in the 1960s to find jeans that fit. Dickson likes to talk about the first Gap store on Ocean Avenue, in San Francisco’s Ingleside neighborhood, where the Fishers sold “jeans, records, and tapes. That was it,” he says, his eyes widening and his voice dropping to a whisper.
As Dickson sees it, the brand lost its way when it veered from that utilitarian principle, chasing fast-fashion trends and sacrificing quality. “People come to us for classics: khakis, denims, white T-shirts.” He thinks the company should “lean into those. Make them special. Do collaborations with people that reinvent them in ways that make them surprising.”
In February, Dickson brought on fashion designer Zac Posen as creative director of Gap Inc. and chief creative officer of Old Navy. The hire came as a surprise to many. Runway designers don’t generally succeed in mass retail, though Posen has spent time at Brooks Brothers and Delta (he designed a collection of plum-colored, vaguely retro flight attendant uniforms). Mark Breitbard, who heads up the Gap brand, says, “It’s been great having his energy and creativity in the building. It’s not necessarily about, okay, now he’s going to go work on this specific design—it’s a thought partnership.” He added that Posen also brings his “relationships—he’s a great resource on collabs.”
Also in February, Dickson offered his first real hint at how he and his team plan to make basic clothes enticing: the “Linen Moves” campaign, stemming from an uptick in linen sales. Reminiscent of the Gap’s legendary “Khaki Swing” commercial from 1998, the online ad was a honey-hued video set to electronic music group Jungle’s “Back on 74,” with a group of dancers, led by singer-songwriter Tyla, replicating the choreography from the song’s viral music video. The hip-swiveling performers are decked out in muted-tone basic Gap pieces, but the look—crop tops and billowing, low-slung pants—is anything but preppy.
“We didn’t style them,” insists Dickson. The crew merely hung up the clothes on racks and let the dancers choose. He had told the creative team just to “leverage music”—a nod to those old records and tapes in that original Gap store. The campaign racked up more than a million YouTube views. Dickson calls it “a new expression of the brand’s purpose, the beginning of a new beginning.”
Unlike Mickey Drexler, The Gap’s “merchant prince” CEO who shaped the company through its glory decades and went on to replicate his success at J.Crew in 2002, Dickson hasn’t spent his career forecasting clothing trends and analyzing supply chain efficiencies. But he’s not merely “the Mattel guy” either.
Dickson was raised in the clothing business. It’s something he rarely discusses, and when he does, he grows uncharacteristically reserved.
All four of his grandparents were Holocaust survivors. His maternal grandmother had been sent to Auschwitz, and “she survived by sewing,” he says, “essentially kind of fixing the uniforms of. . . .” His voice trails off.
Dickson says that his maternal grandfather fought in the resistance in Eastern Europe and “became kind of a mechanic, finding things he could repair.”
They eventually set up a fashion business in New York’s Garment District. Dickson says his grandfather ran the machines that manufactured his grandmother’s clothing. “I remember watching my grandmother design, [and] sitting by the sewing machines with her. It was women’s clothing, almost couture. It was sold,” he says with pride, “at Saks.”
Dickson’s parents carried on the tradition. His mother was the president of Aca Joe stores in New York City; the retail chain had a Gap aesthetic in the ’80s, selling T-shirts and casual clothing. Dickson worked in the stores on weekends—“cleaning toilets, folding T-shirts in the stockroom,” he says. When his dad became CFO of Ellen Tracy, the younger Dickson worked in warehouses where that clothing was stocked. His father later became CFO and COO of Calvin Klein.
After graduating from the University of Maryland in 1990, Dickson entered the executive training program at Bloomingdale’s, pumping life back into the kids’ department, winning the men’s fragrance buyer of the year award, and launching Off Bway, a division for indie cosmetics. He left to cofound Gloss.com, a cosmetics e-commerce company that was acquired by Estée Lauder in 2000. Then came a call from Mattel. It needed someone to expand Barbie beyond toys. “Mattel was a disaster” at the time, Dickson explains. “They’d just lost their CEO. The stock was terrible.”
[carousel_block id=”carousel-1721237063575″]Dickson came in as general manager and senior vice president and stayed for 10 years. Then, after decamping to run struggling apparel conglomerate the Jones Group, which was sold to private equity in 2014, he returned to Mattel as president and COO to continue his work on Barbie, which had floundered in his absence. “People were like, you’re crazy, you’re in a great spot. Toys are going down, digital gaming is taking over, kids are on screens, Barbie is irrelevant. Give it up.”
Having already revamped Barbie’s online presence and extended the brand into entertainment, including direct-to-TV movies, Dickson forged creative partnerships with non-toy brands; an early one with Bloomingdale’s took place during New York Fashion Week. He also launched Mattel Creations as a direct-to-consumer platform for collectibles, enlisting artists such as Mark Ryden and furniture designers like Kartell to come up with Barbie collections. Most importantly, he recast Barbie as an accessible icon rather than an impossible ideal, introducing dolls of various ethnicities and body types. The original logo returned, and the 200-plus shades of pink that had made their way into Barbie products were nixed for just one: Pantone 219.
When it came to the movie, Dickson “was the brand steward, the brand ambassador,” says Robbie Brenner, head of Mattel Films. “All of the barriers he broke with Barbie—the notion of female empowerment and representation—are directly correlated to the film.”
Dickson knew there were risks. “We were giving our IP over to these geniuses,” he explains, and then after filming, “they get to go, like, ‘Movie over!’ and we have to stay here.” He and his team, therefore, worked hard to make sure that “every fashion piece, every outfit, every car, every architectural part of Barbie world was done through the Barbie brand ecosystem.”
This also entailed close script attention and, at one point, a sudden trip to the set in London to debate a scene with Gerwig and Robbie that he felt tarnished Barbie’s image. When the director and star acted out the scene for him in person, “it was a totally different feeling,” he says. The scene remained.
Dickson may be drawn to pain, but he got a more than ample helping of it when he arrived at Gap Inc. in 2023. During the years before his arrival, under interim CEO Bob Martin, the company had gone through what Breitbard calls “the brutal cleanup” following a pandemic-era spiral. There were massive layoffs, store closures, and a restructuring of international markets. Company culture was broken. It was “a fragmented organization that had different experiences under different leaders,” Dickson says. “The purpose, the mission, the vision—what holds a company together—was not strong.”
Richard DicksonI call it putting candy in the road. You don’t have to see the end result yet. But if you can see two or three steps of where I’m trying to get to, that’s good enough.”
Dickson began implementing a work environment where “uncomfortable conversations are now less uncomfortable,” he says. There are more frequent town halls and new “what’s on my mind” dialogues, and employees are more empowered. (When Dickson dropped in on one Gap store, he was chagrined to find the music blaring; when he asked the staff why they hadn’t turned it down, they said that the volume-level directive had come “from corporate.”)
“I call it putting candy in the road,” he says of the incentives he’s creating. “You don’t have to see the end result yet. But if you can see two or three steps of where I’m trying to get to, that’s good enough.”
Dickson may need to lay out quite a bit of candy. Historically, new ideas
and individuals—particularly creative directors—have sometimes become stifled by “the straitjacket of Gap,” says GlobalData’s Saunders. “What has always happened is the people eventually left and Gap has continued on its merry way doing what it’s always done. It is a business that has been reluctant to change, and it has had an apathetic and quite arrogant culture.”
One executive who collaborated with Gap Inc. for several years describes it as a “run it up the flagpole” environment, where ideas got watered down, or entirely cast off, once they were passed to higher-ups for approval. “Orders would come down and everything would have to be changed at the last minute, at great expense and with no great vision.”
Having the Fishers involved adds another layer of complexity. “Their seal of approval is needed for a lot of things,” Saunders says.
This may bode well for Dickson, who often shares meals with the family and rather enjoys hearing Fisher grandkids’ blunt feedback. “They say the truth,” Dickson says. “We should be better than we are.”
In the meantime, he’s moving forward. If you tell him you’ve noticed a difference in the Gap’s website, he lights up. “Really? You see!” he says, beaming. Visual clutter and in-your-face pricing discounts have been cleared out. And don’t get him started on the Old Navy site. “There was so much stuff coming at you! It was 50 off, 40 off, buy this, buy that. . . . At the end of the day, we pay you!” he jokes. “It’s unbelievable.”
The company is also reducing inventory so that stores don’t come across like discount outlets. But Dickson’s bigger vision involves harnessing the Gap’s consumers and turning them into something more. “For a company like ours that has a database of over 50 million households, one could argue that’s a media company,” Dickson says. “We could leverage that relationship to be much more personal.”
What might that look like? “Community,” he says. When the people visit the site today, “it’s not actually a dialogue. I’d like to make it a dialogue.”
Meanwhile, signs of a turnaround are emerging. In the first quarter of 2024, all four Gap brands saw sales increases, something that hasn’t happened in more than a decade. Company-wide, sales rose 3%—more than the 1.2% Wall Street had anticipated. The news sent Gap stock up 20% in the hours after its earnings call in late May. Remarkably, a few days later, the company’s market share hit $11 billion, nearly quadruple what it was when Dickson first arrived.
On the design front, a recent collab with Dôen turned millennial women’s heads, as did a white Gap shirtdress ensemble that Anne Hathaway wore to an event in Rome. And retail nostalgia is also on the Gap’s side. “Ralphcore” is officially a trend as Gen Zers embrace Ralph Lauren’s preppy aesthetic, and CEO Fran Horowitz has orchestrated a dramatic turnaround at Abercrombie & Fitch. “There’s a great deal of interest, culturally, for all things ’90s,” said Erik Maza, executive style director at Town & Country. “People are returning to these labels that had maybe fallen out of favor.”
It’s important to Dickson that the Gap reenter the cultural conversation. This happened in May when Oscar winner Da’Vine Joy Randoph showed up at the Met Gala in a Gap denim gown custom designed by Posen—who also attended the event, in a Banana Republic suit.
The next day, Dickson posted a photo of the two to LinkedIn, referring to the dress as “an homage to denim . . . and a tribute to the flowing waters of the San Francisco Bay.” Though it had been well received in the fashion community, a couple of commenters griped that the dress didn’t sufficiently evoke the gala’s 2024 theme, “Garden of Time,” and it’s true that the dark cascading denim didn’t exactly scream “flora.” What it did evoke was history.