This week, Gap released a new ad for its denim line featuring girl group Katseye dancing to Kelis’s “Milkshake.” The ad is undeniably fun to watch (and rewatch) and has gone viral online with an outpouring of positive responses. There’s a lesson here: playing it safe and sticking to a formula that works — while adding a trendy twist — pays off.
Gap’s competitors, American Eagle and Lucky Brand, also recently released celebrity-endorsed ads — but with Sydney Sweeney (to some, ahem, controversy) and Addison Rae, respectively. My colleague Jordan Hart reports that the social media engagement on Gap’s Katseye ad was far ahead of its peers, and it was clearly winning the back-to-school jeans war.
The Gap has been creating visually and thematically distinctive ads — models, sometimes celebs, singing or dancing against a monochromatic backdrop since the late ’90s. It’s a template that’s distinctive and has worked — and the latest Katseye ad is hitting a particular sweet spot of throwback and zeitgeist.
Let’s take a walk down memory lane, shall we?
1998: Swing khakis. If you weren’t around to remember this, just trust me: this ad of people dancing in tan pants to “Jump, Jive, an’ Wail” was huge. It hit on a weird microtrend moment of a swing dancing revival in the late ’90s, and there’s even some new-at-the-time “Matrix”-style camera effects! This turned out to be one of the most iconic TV ads of the decade — and Gap was very happy to iterate on it.
1999: Mellow Yellow cords. This time, instead of dancers, the ad features bored-looking models (look out for a young Rashida Jones) singing the 1966 Donovan song “Mellow Yellow”.
2001: Daft Punk and Juliette Lewis. Celebrities start getting into the mix now. At the time, neither Juliette Lewis nor Daft Punk were huge superstars, but both had some cool credibility that made the ad work — it made Gap jeans seem cool. (This is maybe a personal favorite? A friend recently revealed he could do the entire Juliette Lewis dance from memory, which is a great party trick).
2002: “Love Train” holiday stripes. The striped skinny scarf era gives me hives to look at (both thinking about and remembering the itchiness). At this point, the ads were comfortable and predictable, like a Gap sweater.
2003: Into the Hollywood Groove. Madonna and Missy Elliott performed in an ad where Madonna sang a mashup of “Into the Groove” and “Hollywood.” For me, this doesn’t quite land — it’s hard to believe either Madonna or Missy Elliott, both known for their distinctive personal style, wear clothes from the Gap.
2004: Sarah Jessica Parker and Lenny Kravitz. This came out just a few months after “Sex and the City” ended, and Sarah Jessica Parker was a huge star with a ton of fashion credibility (she somehow makes a fedora work here).
This goes on and on. In the last few years, there have been ads with Tyla and Troye Sivan, and this spring, with Parker Posey — right at the peak of her “White Lotus” fame.
And yes, there were some years when the Gap was a little lost in the wilderness — particularly in the early aughts — and probably wanted to move away from these ads to feel fresh (let’s never mention the disastrous logo rebrand).
The rise of fast fashion put the screws to it, and in the last decade, it’s gone through some corporate reshuffling.
There’s always been a slightly evolving question of what the Gap is, and who it is for. Is it plain basics for everyone? Boring soccer mom clothes? Trendier items to appeal to younger shoppers? More designer-y stuff for a sophisticated crowd?
For now, it seems the Gap is experiencing a moment in the sun. It has a new CEO, former Mattel executive Richard Dickson, who started in 2023 and brought on designer Zac Posen as creative director. Its sales for the first quarter of 2025 were up, although it predicted flat growth for the spring and summer, citing tariffs. But overall, things are looking pretty good for the Gap.
The Katseye ad hits just at the right moment. The group, which formed on a competition show from K-pop label Hybe, is incredibly popular right now. They’re also capital-F fashion — they recently starred in ads for Fendi. They’re good dancers, and they make the baggy jeans and denim miniskirts look cool and hip. Using the 2002 song “Milkshake” instead of one of Katseye’s own songs makes sense when you look at the legacy of throwback songs like “Mellow Yellow” in Gap ads. Plus, everyone loves “Milkshake.”
The ad isn’t risking anything new; it’s sticking to a formula that it knows works. The little extra flair it’s adding is the choice of celebrities in the zeitgeist, and making it fun to watch and rewatch. This isn’t too far from what makes the Gap’s clothing appealing: it’s safe, familiar, reliable — you know exactly when you walk into a Gap store, you get a striped tee or a pair of jeans — but with a faint whisp of trendiness that makes it work.
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