GAP’s Fall Campaign Bets on Baggy Nostalgia

THE SIGNAL

The Play

GAP is going oversized. The retailer’s new Fall 2024 campaign features Troye Sivan and Thundercat styled in slouchy hoodies, wide-legged khakis, and denim jackets with exaggerated volume. The campaign, which debuted August 21, pairs fashion with music in a way that taps both nostalgia and current culture. According to Marketing Dive, GAP’s new direction celebrates individuality through “the creative spirit of music and style.” It’s part of a broader attempt to make GAP culturally relevant again with Gen Z and younger millennials.

The Context

The aesthetic GAP is chasing is not new. It is a deliberate throwback to early 2000s silhouettes: wide fits, washed-out colors, and volume as a statement. But the timing of the campaign shows smart alignment with fashion media’s current analysis. A recent piece in Harper’s Bazaar detailed how oversized clothing has outlived its streetwear roots and become a core trend across runways and casual wear alike. From Balenciaga’s theatrical proportions to skate culture’s baggy jeans, the oversized look has become a coded signal for cool.

GAP has often hovered on the edge of this trend without fully committing. Its late-90s and early-2000s heyday defined basics like hoodies, cargo pants, and denim jackets that now feel current again. What’s different in this campaign is the casting and attitude. Troye Sivan brings queer pop credibility and a strong visual brand, while Thundercat embodies experimental style and genre-bending music. Both artists represent a modern version of “GAP cool” that leans into identity expression, not just American classics.

The campaign arrives at a moment when legacy retailers are fighting for cultural cachet. GAP has seen sales declines in recent years, particularly among younger consumers. The brand is trying to recapture cultural capital by positioning itself at the intersection of music, fashion, and identity. It is also likely hoping to mimic the viral momentum that brands like Loewe and Diesel have generated through bold creative campaigns and smart talent curation.

The Takeaway

GAP’s move signals more than just a seasonal aesthetic shift. It reflects the larger push by traditional brands to reenter conversations that are increasingly driven by creators, stylists, and niche fashion communities. By aligning with a trend that already dominates social feeds and music videos, GAP is trying to embed itself inside the algorithm, not outside of it.

• Format-forward casting: Troye Sivan and Thundercat are not just famous—they each represent a distinct audience and visual culture. Sivan’s fashion-forward persona plays well on TikTok, while Thundercat’s eccentricity brings an edge that GAP has not explored in recent memory.

• Trend timing over trendsetting: Rather than inventing a new look, GAP is strategically embracing a trend that is already validated by fashion media and streetwear. This reduces risk and increases resonance.

• Cultural rebirth or campaign blip? For GAP to succeed, this campaign needs to be more than an aesthetic shift. It must be followed by distribution improvements, digital experience upgrades, and consistent cultural alignment—not just a well-styled moment.

• Fashion’s mood is getting louder: With oversized silhouettes here to stay, legacy brands must decide whether they are willing to evolve with the aesthetic. Playing it safe no longer guarantees relevance. Playing it big might.