Gap Inc. is betting big on entertainment as a path to cultural relevance, creating a new chief entertainment officer role dedicated to what it calls "fashiontainment,” a strategy that blurs the lines between content creation and commerce through partnerships across music, film, sports, and gaming.

"CEO Richard Dixon has been tasked with reinvigorating the Gap brand, as well as the other brands, Old Navy, Banana Republic, Athleta," said our analyst Sky Canaves on a recent "Reimagining Retail" episode. The move follows Dixon's successful turnaround at Mattel, where the "Barbie" movie became a cultural phenomenon that drove brand affinity and sales.

The new role sits above individual brand marketing teams, which will continue to handle creative vision, product direction, and campaigns for Gap, Old Navy, Banana Republic, and Athleta. This creates a high-level position focused on building partnerships and cultural moments rather than day-to-day marketing execution.

Recent successes hint at the potential.

• Gap's collaboration with K-pop group Katseye went viral, surprising even the company with its reach.
• Other moments included a denim ballgown at the Met Gala, an Anne Hathaway dress that generated social buzz, and a White Lotus collaboration with Banana Republic.

"The role of the chief entertainment officer will be to think more broadly and how to link those viral moments to create a cohesive brand narrative or strategy that can capitalize on viral moments, but isn't solely dependent on them," Canaves said.

The tension between entertainment and marketing

The distinction between a chief entertainment officer and a chief marketing officer remains unclear, raising questions about whether this is truly transformational or just another C-suite title variation.

"We've seen chief brand officers, chief digital officers, chief creative officers, chief growth officers, chief customer officer," said our analyst Blake Droesch. "This move runs the risk of being added to the long lineage of CMO adjacent C-suite jobs that aren't, at the end of the day, super entirely distinct."

The press release announcing the role specified that brand teams will continue leading creative vision and campaigns, suggesting the entertainment officer operates at a strategic level above tactical execution.

• But without clear boundaries, the role could overlap significantly with traditional marketing responsibilities.
• Retailers experimenting with new organizational structures must clearly define roles to avoid confusion and ensure the investment delivers measurable impact beyond headline-grabbing announcements.

Why Gap needs entertainment to compete

Gap faces intensified competition from online brands, dupes, and dispersed shopping channels that make maintaining customer loyalty increasingly difficult for mid-market mass brands.

"It's a fashion brand and there's so many fashion options,” said Canaves. “[Staying relevant] becomes ever more important for a brand like Gap that's a mid-market mass brand. It risks falling into the middle of not very special or casual brands that don't have a strong brand identity."

The company has shown momentum under Dixon's leadership, but growth has come primarily from value-focused Old Navy rather than the flagship Gap brand, which still needs to strengthen its core retail fundamentals alongside its entertainment ambitions.

“They still do have a lot of work to do in improving just the relevancy of the products that they offer and not to mention the online shopping experience,” said Droesch.

How success will be measured

Measuring the impact of a brand-building role focused on long-term cultural relevance presents challenges, particularly in the first year of a new position.

• "There's going to be one big piece of media that is going to have to emerge from this, whether it's a big partnership with an event like Coachella or a unique partnership with a celebrity that's going to bear the fruit of some sort of content that is generating buzz," Droesch said.
• Potential metrics include media impact value measurements that quantify campaign buzz, unaided brand awareness, brand affinity, new-to-brand customers, and ultimately sales growth for the Gap brand specifically.

The company will need to demonstrate that the investment justifies the expense of a new department and LA office, likely requiring at least one major cultural moment that drives measurable business impact.

While Gap’s scale may justify a standalone C-suite entertainment role, its ability to prove out the model will serve as a bellwether for how retailers of all sizes approach entertainment as a brand-building lever.

"Every brand should have a brand-building content strategy that has a strong entertainment or cultural component, whether it's capital 'E' entertainment like a Hollywood film or just telling brand stories through micro- and nano-influencers," Canaves said.

Listen to the full episode.

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