TOMS CEO Drives Digital-First, Nostalgia-Fueled Brand Revival

Watch more: Inside the Next Chapter of Brand Building at TOMS

Some brands become iconic, embedding themselves into culture, closets and conversations.

But even the most recognizable names eventually reach a moment when they must refresh, reintroduce themselves and reclaim their place in a market that has evolved around them.

That is the moment TOMS now occupies, and CEO Jessica Alsing told PYMNTS CEO Karen Webster in an interview for “The SKU” series that the goal is to lead the brand into a new chapter built on clarity, modern execution and deeper connection.

TOMS’ Footwear Niche to Iconic Status

TOMS has long occupied a distinct space in footwear. The brand is known to be simple, casual, recognizable and purpose-driven. It sits alongside brands such as Birkenstock that have maintained cultural staying power across generations.

The market is experiencing renewed excitement for “older Americana brands that were beloved in the past,” such as Gap and Coach, Alsing said.

Beyond its roots as a founder-led company, the TOMS brand rebuild is being framed as a reintroduction, with nostalgia at its core. Some of the key styles, including the classic alpargata and espadrille styles, are iconic offerings and “the way back in… for what we are known for,” Alsing said.

TOMS is emphasizing digital first.

“Consumers really focus digitally … anyone from 8 to 80 often start a purchase on their phone,” Alsing said.

That includes discovery through social media, creator content, search and eCommerce. At the same time, digital does not replace wholesale.

“People tend to really love to buy shoes, particularly, or footwear, in a multichannel environment,” she said.

The dual channel model means that TOMS can scale the brand and build credibility across fashion and lifestyle verticals, Alsing said.

At the same time, TOMS is revising its wholesale strategy to reflect modern expectations of premium brand positioning. The aim is to create retail environments and partner ecosystems that align with the repositioning, not simply volume distribution, but strategic placement and brand-right context.

While digital discovery dominates, the tactile element of footwear remains critical. TOMS plans to work with wholesale partners to build in-store fixtures, co-marketing and storytelling that deliver the product promise through comfort, style and purpose in physical settings, even as digital remains central.

Unaided Awareness and Intentional Nostalgia

The nostalgia is intentional. The company benefits from “tons of unaided brand awareness” and a “Venice Beach heritage,” Alsing said, describing it as “projecting effortless, endless summer style… it’s [a] really casual lifestyle-type brand.”

Storytelling is at the heart of the repositioning. Alsing said she wants TOMS to step into “a creative-led storytelling” model where product and purpose are woven together. As creators “really start to tell the story of our brand… we have real voices that are building credibility in our community.” That includes narrative direction, aesthetic identity and aligning what the brand means next.

Creators will be instrumental to execution.

“What creators can do is to add to the vision of the brand rather than just… market it,” she said.

But there’s also a caution to sidestep what she termed “collaboration fatigue,” so authenticity is key. Partnerships must “come from a place of authenticity… where everyone really… feels the same” about the moment or mission.

She said her ideal collaboration example is with the brand Erewhon, imagining a capsule footwear collection tied to community give-back.

The Role of AI

Artificial intelligence will be part of the repositioning, but in a supporting role. Customers may soon shop via new conversational models, Alsing said.

“Shopping directly in ChatGPT… is a huge opportunity,” she said.

The brand will not be buying solutions with abandon but will instead seek to use the platforms already developing AI and will “feel the windfall of the technology,” she said.

TOMS is entering a new chapter where the aim is not to reinvent everything, but to reconnect what made it special with how consumers shop, brand and engage today.

Alsing said the guiding principle is simple: “Don’t run away from who you are.”