How 1990s icon got its cool back — but will Gen Z buy it?

Dig out your hoodies and dust off your chinos — Gap is making a comeback. The brand, known for its denim, borderline omnipresent khakis and logo-emblazoned hoodies, will follow in Topshop’s footsteps in returning to the British high street for the first time since 2021, with a two-storey shop in London’s Covent Garden opened on Nov.6, and additional stores in Shepherd’s Bush and Wembley to follow. The iconic chain’s revival has been headed by Richard Dickson, the brand’s chief executive since August 2023, who was also the American toymaker Mattel’s president during Barbie’s reinvention, culminating in the Oscar-winning Greta Gerwig film starring Margot Robbie. He's now been charged with returning Gap to its glory days of quality basics.

It was a sad send-off four years ago when Gap, which opened in 1969, retired its physical stores, which bowed out clad in gargantuan sale signs. The retailer, once considered a cultural behemoth, had scored global clout and appeal in the early 2000s, working with the likes of Madonna, Missy Elliott, Lenny Kravitz and Sarah Jessica Parker on hugely successful campaigns. It was known not exactly for fashion, but for reliable comfort at decent prices. From the 1980s onwards it was a stalwart for the best basics, with its “Individuals of Style” campaign, shot by Annie Leibovitz, which celebrated wearing simple clothing your own way. The competition couldn’t get close. But in the last couple of decades the retailer had floundered as fast fashion from the likes of H&M and Zara took over the high street, and rivals like Uniqlo began to make their name.

Gap lost its identity — and it’s only recently that it seems to be finding its footing again. In 2020, there was a failed Kanye West collaboration that concluded after just two years when the rapper made a string of antisemitic comments. Gap sued him for $2m (£1.5m) a year later for unauthorised rental property renovations. Eight months ago, the brand failed to regain its relevance again with a Feels like Gap advertising campaign, featuring White Lotus star Parker Posey dancing in an elevator (her moves were a little clunky, and the internet wasn’t impressed by her mum-after-three-glasses-of-wine moves). But when White Lotus alumnus Sydney Sweeney caused a bigger denim snafu with her “great jeans (genes)” American Eagle ad, which was accused of using the language of eugenics, Gap had the perfect retort.

They produced another dance concept, this time featuring the Los Angeles girl group Katseye, choreographed to Kelis’s 2003 hit single “Milkshake” and dressed in the brand’s latest denim. “Now THAT’S how you do a jeans advert,” one person wrote on TikTok, where the video became the number one search in August, with thousands of users learning the routine. “Me on the way to GAP,” another person added alongside a photo of a yellow taxi cab soaring over a speed bump underneath the video. “Wait for me!!” read further replies.

Last night, Gap struck another pop culture chord with the release of its Christmas campaign starring Gen Z’s answer to Adele, Sienna Spiro, whose track “Die on this Hill” is currently trending on TikTok and in the number 16 spot in the UK charts. The 20-year-old singer belts out an acoustic cover of Miley Cyrus’s Hannah Montana: The Movie hit “The Climb” backed by a choir clad in Gap’s knitwear. “Suddenly I wanna buy Gap,” one person admitted underneath the post. It was, the comments concluded, a “slay”.

Gap’s overall social media strategy has been directed at the 18-29 demographic in recent weeks. They’ve hired influencers to make “fit check” videos in elevators, filmed on the iPhone’s zoomed-out 0.5 setting, beloved by the young since 2022. In the last week, they’ve gone from roughly 1,000 likes a post to averaging around 5,000, with this number hitting 45,000 in under 24 hours for their Christmas ad.

When the brand collaborated with Sandy Liang (the New York designer beloved by Rosalía, Jennie Kim, Ariana Grande and Bella and Gigi Hadid) on trench coats, fur-cuffed denim jackets and poplin Peter Pan collar shirts earlier last month, it turned fashion fans’ heads. “I’m actually losing my mind over the fur trucker jacket,” one person wrote. “Oh hell yeah,” another person echoed. No elaboration needed.

Dickson has made sure to continue this elevated couture-coded energy by hiring fashion heavyweights in key roles, such as Kate Spade’s chief merchandising officer Michele Parsons and Reed Krakoff from Coach, who has taken over accessories. That side of the operation has already grabbed attention on Instagram with its Gap teddy bear and mini tote bag charms in the same way as Pop Mart’s keychain gremlin doll Labubu captured shoppers’ hearts. Meanwhile, John Demsey of MAC Cosmetics will be on beauty for the brand.

There is also the elevated (pricier) GapStudio collection, designed by Zac Posen of Project Runway fame and modelled by Gwyneth Paltrow alongside her daughter, 21-year-old Apple Martin. Pieces have also been spotted on Lila Moss (Kate Moss’s 23-year-old daughter), Dune star Timothée Chalamet and Adolescence actor Owen Cooper, who became the youngest male actor to win an Emmy this September.

Still, getting normal shoppers to visit Gap stores may not be easy. More than 70 per cent of people said the retailer no longer resonates with modern consumers, according to research conducted by Harris Poll UK.