How Gap’s new ad campaign signals CEO Richard Dickson’s brand strategy

If you grew up shopping at Gap, you can likely remember some of the great moments in its brand marketing history, from ads featuring a young Spike Lee in the 1980s to the slogan “For every generation” to the famous “Who Wore Khakis” series of print ads, featuring unexpectedly preppy styling from the likes of Miles Davis, Picasso, and James Dean. But it’s been a while since the Gap brand really crossed over to enter the sweater-buying pubic’s consciousness—a loss in cultural cachet that has run in parallel with diminishing financial success. For the 12 months ending in October, the entire company’s net sales slid by 7%, while Gap net sales were down 15%. (Gap Inc. also owns Athleta, Old Navy, and Banana Republic.)

The financial sluggishness—and underlying creative torpor—are what new-ish Gap Inc. CEO Richard Dickson was hired away from Mattel to change. Dickson, who oversaw the Barbie brand’s renaissance, had previously served on Gap Inc.’s board of directors, so he was perhaps more familiar with the brand than most incoming executives. “Gap was was best at its really being about a true original. It was a pop culture brand, and it did more than just sell clothes,” Dickson tells Fast Company. “We were really great at it—until we weren’t. That’s really where I would say Gap hasn’t lived up to its legacy and its potential.”

Under new leadership, which will include Dickson, Gap brand CEO Mark Breitbard, and Zac Posen, whom Dickson recently tapped to be the brand’s creative director, a major effort to revive Gap’s fortunes is underway. And as part of that initiative, the brand is unveiling a slick new campaign, one that offers a callback to the brand’s heyday while also trying to articulate a sensibility for the future. Starring Tyla, the South African recording artist who just won a Grammy, the ad also features Jungle, the YouTube-famous British electronic music group whose work has been used commercially by Apple, Starbucks, and EA Sports. The video, below, is vaguely reminiscent of Gap’s “Khakis swing” TV commercial from 1998, except where that spot was decidedly retro, this one features a crew of dancers sporting slouchy Gap linen and sexy crop tops, all shot in one continuous take.

What are we to conclude from this work? “Improved photography, styling, tighter assortment, better storytelling,” says Breitbard in listing the new campaign’s attributes. It’s also worth noting that Gap is going digital-first with this campaign, focusing its spending in particular on YouTube to reach, potentially, a generation of consumers who may be much more familiar with Tyla’s music than, say, they are with nostalgia for the mall brands their parents grew up with. “The talent that we have with Tyla and Jungle and the popularity that we’re going to drive for both of their personas through this campaign really expresses what we call relevance,” Dickson says. “And from there, you’re going to see the experience come alive in our stores and online.”

Whether Tyla will help Gap unlock a new chapter of cultural relevance and business success remains to be seen. “I’d say we’re getting our vibe back and importantly we’re starting to matter again and be part of the cultural conversation,” says Dickson. “But recognizing this is really just the start—the beginning of a new beginning.”

Still, it’s worth noting that Dickson’s bet on an ad campaign, as an expression of his vision as a new CEO, comes at a moment when brands ranging from Ikea to Dunkin to Verizon also are taking some pretty ambitious swings with splashy ad campaigns. Could this be the beginning of a mini trend back towards the creative? At a time when the advertising industry is under tremendous pressure, and after years of marketers allocating ever more budget to influencers and lead gen campaigns that promise efficiency at scale (and now AI!), it is nice to see iconic corporate bellwethers like Gap Inc. try to craft a compelling message and take it to the people. If creativity and style again inform the advertising we absorb every day, that would be, like the Tyla Gap ad, both a throwback to an earlier era and—maybe, just maybe—something that feels really fresh and full of energy for today’s consumers.

If you grew up shopping at Gap, you can likely remember some of the great moments in its brand marketing history, from ads featuring a young Spike Lee in the 1980s to the slogan “For every generation” to the famous “Who Wore Khakis” series of print ads, featuring unexpectedly preppy styling from the likes of Miles Davis, Picasso, and James Dean. But it’s been a while since the Gap brand really crossed over to enter the sweater-buying pubic’s consciousness—a loss in cultural cachet that has run in parallel with diminishing financial success. For the 12 months ending in October, the entire company’s net sales slid by 7%, while Gap net sales were down 15%. (Gap Inc. also owns Athleta, Old Navy, and Banana Republic.)

The financial sluggishness—and underlying creative torpor—are what new-ish Gap Inc. CEO Richard Dickson was hired away from Mattel to change. Dickson, who oversaw the Barbie brand’s renaissance, had previously served on Gap Inc.’s board of directors, so he was perhaps more familiar with the brand than most incoming executives. “Gap was was best at its really being about a true original. It was a pop culture brand, and it did more than just sell clothes,” Dickson tells Fast Company. “We were really great at it—until we weren’t. That’s really where I would say Gap hasn’t lived up to its legacy and its potential.”

Under new leadership, which will include Dickson, Gap brand CEO Mark Breitbard, and Zac Posen, whom Dickson recently tapped to be the brand’s creative director, a major effort to revive Gap’s fortunes is underway. And as part of that initiative, the brand is unveiling a slick new campaign, one that offers a callback to the brand’s heyday while also trying to articulate a sensibility for the future. Starring Tyla, the South African recording artist who just won a Grammy, the ad also features Jungle, the YouTube-famous British electronic music group whose work has been used commercially by Apple, Starbucks, and EA Sports. The video, below, is vaguely reminiscent of Gap’s “Khakis swing” TV commercial from 1998, except where that spot was decidedly retro, this one features a crew of dancers sporting slouchy Gap linen and sexy crop tops, all shot in one continuous take.

What are we to conclude from this work? “Improved photography, styling, tighter assortment, better storytelling,” says Breitbard in listing the new campaign’s attributes. It’s also worth noting that Gap is going digital-first with this campaign, focusing its spending in particular on YouTube to reach, potentially, a generation of consumers who may be much more familiar with Tyla’s music than, say, they are with nostalgia for the mall brands their parents grew up with. “The talent that we have with Tyla and Jungle and the popularity that we’re going to drive for both of their personas through this campaign really expresses what we call relevance,” Dickson says. “And from there, you’re going to see the experience come alive in our stores and online.”

Whether Tyla will help Gap unlock a new chapter of cultural relevance and business success remains to be seen. “I’d say we’re getting our vibe back and importantly we’re starting to matter again and be part of the cultural conversation,” says Dickson. “But recognizing this is really just the start—the beginning of a new beginning.”

Still, it’s worth noting that Dickson’s bet on an ad campaign, as an expression of his vision as a new CEO, comes at a moment when brands ranging from Ikea to Dunkin to Verizon also are taking some pretty ambitious swings with splashy ad campaigns. Could this be the beginning of a mini trend back towards the creative? At a time when the advertising industry is under tremendous pressure, and after years of marketers allocating ever more budget to influencers and lead gen campaigns that promise efficiency at scale (and now AI!), it is nice to see iconic corporate bellwethers like Gap Inc. try to craft a compelling message and take it to the people. If creativity and style again inform the advertising we absorb every day, that would be, like the Tyla Gap ad, both a throwback to an earlier era and—maybe, just maybe—something that feels really fresh and full of energy for today’s consumers.