For four decades, J. Crew has built its identity around preppy staples—cashmere cardigans, tweed jackets, and classic wardrobe pieces that have drawn high-profile fans including Michelle Obama, Demi Moore, and Meghan Markle. Across that history, which spans the brand's origins as a catalog through its growth into a physical and omnichannel retailer, styling decisions have been made by humans. As of Wednesday, artificial intelligence is joining the effort.

J. Crew announced the launch of Style Advisor, a consumer-facing, AI-enabled tool that runs on a collection of Anthropic's models. The tool is trained on data from thousands of outfit pairings featured in the company's photo shoots, along with J. Crew's styling principles and pairings of outfits and accessories.

"It's not just about the piece that you're looking for, but how to style it," said Danielle Schmelkin, chief information officer at J. Crew. "What those stylists bring to the table—and really recommend more than just the item that you may have picked up when you walked into the store—we are really looking to create that online."

The launch arrives amid a broader shift toward agentic shopping. More than 50% of global consumers have used AI to buy goods within the past three months, and AI shopping tools have proliferated rapidly: Meta Platforms offers its Muse agent, Amazon has introduced Alexa for Shopping, and retailers including Lowe's, Ulta Beauty, and Macy's have rolled out AI shopping assistants of their own.

Adoption of retailer-built assistants, however, still trails general-purpose AI. While 56% of consumers say they use AI chat or search tools such as Anthropic's Claude or OpenAI's ChatGPT, only 27% are gravitating to retailer-created AI shopping assistants, according to consulting firm McKinsey. That gap is the backdrop against which launches like Style Advisor arrive: brand-built tools are competing for attention that general-purpose chatbots already command.

"I think the visual piece is really important," said Schmelkin, describing the distinctive edge she expects Style Advisor to deliver.

The tool is also grounded in contextual details, asking questions to better understand a shopper's intent. If a J. Crew customer told Style Advisor they were looking for an outfit to attend a wedding in Miami, for instance, but not one too formal, the tool would tailor its recommendations to those nuances. In the future, the tool is expected to pull in data from a shopper's past purchase history, enabling even more personalized recommendations and replicating what is already possible during the omnichannel shopping experience.

Style Advisor will debut on J. Crew's desktop website and is expected to be added to the retailer's mobile app at a later date. Those planned steps—the mobile app rollout and the eventual purchase-history integration—are the next milestones to watch as Style Advisor moves beyond its desktop debut.

Under the hood, Style Advisor runs on a variety of Claude models, each assigned a distinct role. Claude Fable 5.1 handles the more complex and ambiguous judgment that allows the tool to think and respond like a stylist. Claude Sonnet 5.5 and Claude Haiku 4.5 support the speed and efficiency of the back-and-forth responses between consumers and the AI stylist, while J. Crew's team used Claude Opus 5.5 to build a working prototype.

"What is the actual experience that we want the shopper to have, and then, how do we think about making sure that we're mapping the right models to be able to deliver that," said Lauren Collett, Anthropic's enterprise go-to-market leader.

Schmelkin said J. Crew built a back-end observation layer that allows the retailer to closely monitor costs. "We want to make sure we are constantly refining and using these models in the right way, both in terms of the outputs for our customers, but also the efficiency we want to see to make this scalable," she said.

Style Advisor also emerged from a wider internal push to drive AI adoption at J. Crew. The retailer has created an AI fluency program that begins with the basics and advances up through vibe coding, and it operates an internal AI lab called "Second Thread," which started with just the tech team but has broadened to include all corporate employees who discuss AI use cases and propose technology solutions. For four years, J. Crew has also run a two-day tech summit featuring workshops, hackathons, guest speakers, and vendor presentations—a program initially limited to the tech team but more recently democratized across the company. Employees are also encouraged to use AI enterprise tools from Anthropic and OpenAI.

The Style Advisor itself was conceptualized by a J. Crew digital product designer, who developed a working prototype before engineers were pulled into the project. The fact that the tool was not mandated from the top of J. Crew's C-suite reflects Schmelkin's efforts to encourage employees to chart their own path on AI.

"I've been screaming to anyone who will listen for years now to get in there and build a habit," Schmelkin said. "You have to find your a-ha moment and then all of a sudden…this could really change the way you think about your own life, work, and team productivity."

For a brand whose styling has been guided by humans for four decades, Style Advisor marks the moment when J. Crew's internal AI groundwork—its fluency program, its Second Thread lab, its company-wide tech summit—extends directly to the shopper.

By John Kell; this story was originally published on Fortune.com.