Gap’s attempted renaissance under Richard Dickson is a mix of legacy, ambition, and tension between new initiatives and legacy challenges. The brand’s pursuit of relevance through “dream team” hires and high-profile category expansions, especially into beauty and accessories, is both bold and fraught with risk. This is particularly true as the core apparel business remains stuck in a cycle of excessive promotions and diluted brand storytelling, even as comps have turned positive. There remains much to be fixed before Dickson turns his gaze to other highly competitive categories, and even then, it’s questionable that the Gap has the consumer’s nod to enter.
For Old Navy or Gap, it’s a risky strategy to assume consumers will meaningfully find beauty or accessories as essentials. And the bigger risk is investing in these new categories before fixing foundational product and price discipline.
Dickson’s Strategy: Big Bets and Bigger Distractions
Dickson has had the Midas Touch. He was an alchemist at Mattel with Barbie, and now he is trying to work his marketing genius at Gap on numerous fronts. But we think his gold may turn to brass if his gaze is diverted. It’s a stretch for his dream team to execute while all the necessary corrections at the Gap family of brands are underway.
As for that team, the recent influx of industry talent—plucked from the likes of Nordstrom (Deb Redmond)), Kate Spade (Michele Parsons), Coach (Reed Krakoff), and Estee Lauder (John Demsey)—is making headlines reminiscent of when luxury houses debuted new creative directors. But the impact for Gap is more for the benefit of Wall Street than Main Street. In Krakoff’s case, he partnered with Lew Frankfort to create the accessible luxury handbag category at Coach over 25 years ago, truly a remarkable feat. Today’s handbag market is considerably more flooded with competition; to transform Gap into a covetable handbag brand will take years if it’s even doable. Frankly, I am a bit surprised by Krakoff’s decision to lead this undertaking, given his career in luxury. He is challenged, in a good way, to create fabulous product at a mass price and live with the constraint of product costs after decades of little if any price constraints at luxury brands. The jury’s out whether the team truly believes in Gap’s product or is on a mission to transform the brand.
Strategic or Distraction?
Skeptics argue that much of Dickson’s rollout—steady press releases, splashy launches, and an influx of executive talent—is a diversionary tactic. Sustainable success comes from product, merchandising, discipline, and taking care of the endless little details—the ethos of the Drexler era: “always on the shop floor” and sweating the fundamentals of retail.
Granted, there is power in collaborations: Exclusivity builds need-to-have, FOMO drives store traffic, influencers create excitement, and star power raises the level of brand heat—at least for a moment. But the steady diet of collabs is not unlike day trading, not investing in the core brand DNA. Dickson’s team is betting that notice-me marketing and operational prowess can restore Gap’s relevance through beauty and accessories.
However, the fundamental question remains whether a celeb-collab strategy makes Gap and Old Navy more covetable and relevant, or merely masks core weaknesses with bright, shiny, new SKUs. For loyalists and insiders, genuine transformation means fixing product first—narrowing assortments, building obsession-worthy classics, and reducing dependence on discounts—not just importing celebrity star power or launching new categories that risk cannibalizing the existing business.
The Gap Experience Disconnect
A tangible tension emerges when contrasting in-store and online experiences. To enter a refreshed Gap store is a totally different experience than to visit Gap.com, where most shopping journeys begin. The stores are pristine and minimalist-inspired, orderly with friendly, newly enthused sales associates happy to assist and offer styling suggestions from the new Gap Studio line. Markdowns are moved to the corner of the store with limited visibility. Moreover, the stores lean into their heritage with iconic personalities and Gap’s musical roots. The stores do not scream promotion.
Online is a different story with promotional race-to-the-bottom offers that often differ by channel, signaling an incoherent brand promise and contributing to shopper frustration. The proliferation of Friends and Family discounting gives 40 percent off at checkout and 50 percent off promotions for virtually everything but Gap Studio and new collabs. These relentless promotions do not romance shoppers with brand storytelling; rather they erode brand equity, breeding transactional shoppers. Constant web-based promotions (with online now accounting for as much as 40 percent of Gap sales), undercut any sense of prestige that beauty or handbags might hope to deliver and undermine any romance store shoppers may engage in.
According to Realytics, an AI-powered performance and consumer analytics firm specializing in offline retail, as of September 30, 2025, Gap’s customer satisfaction lags the broader apparel retail benchmark across all key operational dimensions: Location, Processes, Product, Services, Staff, and Store—except Price, where its CSAT score is on par with the industry average. Among in-store apparel shoppers, “Staff” and “Product” are the two highest-priority drivers of experience, yet Gap significantly underperforms on both. Its Staff CSAT stands at 56 percent versus 80 percent for peer apparel retailers, while its Product CSAT is 77 percent versus the benchmark of 91 percent. These indicators point directly to foundational retail levers Gap must strengthen to reclaim the iconic, beloved brand status it enjoyed three decades ago.
Category Expansion: Capturing Wallet or Cannibalizing Sales?
If Gap’s strategy succeeds, will beauty and handbags capture a greater share of shoppers’ wallets—or just steal spend from apparel? Handbags, in particular, are aspirational purchases often aligned with luxury houses and contemporary premium fashion brands. Shoppers chose handbag brands to signal status, wealth, sophistication and a fashion POV; attributes that mass apparel brands do not provide. Few Chanel, Dior, or even Coach handbag aspirational owners also wear those brands’ RTW; they stretch upwardly for a handbag’s cachet.
For Old Navy or Gap, it’s a risky strategy to assume consumers will meaningfully find beauty or accessories as essentials. And the bigger risk is investing in these new categories before fixing foundational product and price discipline. Gap is expending executive time, investor patience, and shopper goodwill on moves that will arguably drive incremental growth and undermine brand equity and its DNA.
Fall Into the Gap
Gap’s best shot at recapturing hearts and share-of-wallet isn’t through merchandise extensions, but through product and experience that genuinely surprise, delight, and justify value—across every channel. Make the basics extraordinary. Reduce choices, create desire, and focus on coherence, not chaos. As a great merchant famously said, “Making bad, good is harder than making good, better.” Gap has authenticity, heritage and marketing that resonates with lapsed as well as new customers. Now it needs to stick to retail basics, starting with product, product, product.
Gap remains a beloved memory for many—but in its current dance between reinvention and distraction, it must address, “Why should shoppers love Gap again?” The answer never starts with category expansion. It starts and ends with irresistible product.
