GAP is one of the most iconic American retailers of all time. During its peak in the ‘90s and 2000s, it felt like the brand was inescapable, thanks to its well-crafted wardrobe essentials and ubiquitous advertisements with some of the biggest musicians of the era.
In recent years, we have seen GAP reinvigorate itself with a younger, cooler consumer through strategic partnerships with popular streetwear brands like Awake NY and drops with pop stars like KATSEYE.
From LL Cool J’s famous ‘90s TV spot to the brand’s latest collab with KATSEYE, here is A Brief History of GAP’s Greatest Crossover Moments.
Individuals of Style Campaign
When: 1989
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GAP said goodbye to the ‘80s with the Individuals of Style campaign. The ad featured black and white portraits of various celebrities wearing the brand’s items. Some of the most notable models were Lenny Kravitz, Spike Lee, and Whoopi Goldberg. It was fitting way to close out the decade that was full of watershed moments for the brand including expansion outside of the United States and the debut of its iconic blue square logo.
LL Cool J’s Freestyle
When: 1997
This commercial has maintained a legacy to this day for reasons beyond GAP’s clothing. One of the biggest rappers of the ‘90s, LL Cool J, was the leading man in the 30-second ad for Easy Fit Jeans. He used his screentime to show love to one of the biggest independently-owned brands of the time, FUBU. In the know fans immediately recognized the logo on LL’s cap. For the millions unfamiliar, the brand had just been introduced to a whole new audience. It stands the test of time as an excellent example of guerrilla marketing.
Khaki Swing Commercial
When: 1998
It’s tough to make a pair of khakis feel exciting, but that’s exactly what GAP was able to achieve with this iconic ‘90s ad spot. An entire cast of young dancers wore the brand’s signature baggy pants to gyrate around the screen. At the time, the ad also helped fuelled the revival of swing music. GAP’s dancing ads are a formula that the brand still plays with today that has even led to participation from stars like Tyla and Young Miko.
Daft Punk for GAP Denim
When: 2001
Getting one of the most legendary electronic duos of all time to hit the robot in your Canadian Tuxedos is a power play that resonates to this day.
‘Into the Hollywood Groove’ With Missy Elliott and Madonna
When: 2003
By the 2000s, GAP had solidified its relationship with music, and made sure to always be very intentional about it throughout its campaigns. One of its most iconic ads came in 2003. It introduced us to an unlikely partnership between one of the biggest pop stars of all time, Madonna, and arguably the greatest female rapper of all time, Missy Elliott. Before Cher and Future’s duet in 2017, this unexpected crossover set the GAP standard.
Yeezy Gap
When: 2020-2022
GAP’s cultural cachet went a bit dormant throughout most of the 2010s. It received an incredible stimulus package in 2020 with the announcement of Yeezy Gap, a full clothing line designed by Kanye West. In a two-year span, popular items including the puffy Round Jacket and double-layered hoodie were released to much fanfare. In 2021, the line was given a bigger boost when the Yeezy Gap Engineered by Balenciaga collection was announced. Overnight, the classic American retailer was in conversations with one of the hottest luxury brands in the world. As quickly as things ramped up, they ultimately came crashing down. Initially intended to be a 10-year partnership, Yeezy Gap officially ended in September 2022. What could have been.
Dap Gap
When: 2022-2024
Dapper Dan is nothing short of a fashion icon. His coveted custom creations featuring Gucci and Louis Vuitton monograms sparked the logomania trend back in the ‘80s. Decades later, GAP tapped Dap for a surprising collaboration. The signature offering was the ‘DAP’ hoodie, which flipped Gap’s iconic logo hoodie into a tasteful homage. Of course, some of the pieces even featured Dap’s own monogram pattern, a fitting nod to the numerous custom pieces he created in his Harlem boutique. For years, many of us dreamed of owning a Dapper Dan original. His GAP collab made that dream a reality.
Sean Wotherspoon Spearheads GapVintage
When: 2023-Present
GAP has been around since 1969. When you have that much history, there are a ton of amazing items in the archive just waiting to be unearthed. In 2023, GAP decided it was time to tap into the burgeoning vintage space with the help of one of the individuals who helped push vintage clothing to new heights in the 2010s, Round Two co-founder Sean Wotherspoon. As GAP’s global vintage curator, Wotherspoon has built vintage capsules that have been released as part of the GapVintage program available in select stores around the globe.
Awake NY x GAP
When: 2026
As GAP continue to re-establish a foothold in the market, it has looked to streetwear for some help. One of the most recent, and best, collaborations that we have seen from Gap was a partnership with Angelo Baque’s Awake NY. Baque was able to recontextualize some of GAP’s signature pieces through the lens of New York City fashion, while also injecting some streetwear sensibilities into the equation. The capsule collection included highlights like a polka dot denim set and reversible plaid canvas jacket.
KATSEYE x GAP
When: 2026
The latest instalment to GAP’s long history of music partnerships is a drop with the global girl group KATSEYE. The limited-edition collection features six reimagined versions of GAP’s Arch Logo Hoodie that have been personally designed by each member of KATSEYE: Daniela, Lara, Manon, Megan, Sophia, and Yoonchae. The Complex exclusives swiftly sold out upon their release on April 14.
