J. Crew launched an AI shopping tool called Style Advisor on Wednesday, marking the first time in the retailer's four-decade history that styling decisions will be made partly by artificial intelligence. The consumer-facing tool runs on a collection of models from Anthropic, the AI company behind Claude, and is trained on thousands of outfit pairings drawn from the brand's photo shoots alongside its styling principles and accessory pairings.

For 40 years, J. Crew's aesthetic — cashmere cardigans, tweed jackets and other preppy staples — has been curated exclusively by humans, drawing high-profile customers including Michelle Obama, Demi Moore and Meghan Markle. The brand began as a catalog and grew into a physical and omnichannel retailer (selling across digital and store channels). Style Advisor now extends that styling judgment to the digital storefront.

"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."

What does the tool actually do?

Style Advisor asks shoppers contextual questions to determine intent. A customer searching for a wedding outfit in Miami that is not too formal, for example, receives recommendations calibrated to those specific nuances. In a future update, the tool will draw on a customer's past purchase history to sharpen personalization and replicate what is already possible in the omnichannel experience.

"I think the visual piece is really important," Schmelkin said of the edge she expects the tool to deliver. The assistant debuts on J. Crew's desktop website and is expected to reach the retailer's mobile app later.

Which Anthropic models power it?

J. Crew assigned different Claude models to distinct tasks:

• Fable 5.1 handles the complex and ambiguous judgment that lets the tool think and respond like a stylist.
• Sonnet 5.5 and Haiku 4.5 support speed and efficiency in the back-and-forth exchanges between shoppers and the AI.
• Opus 5.5 was used by J. Crew's team to build the 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 to monitor costs closely. "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.

How big is the agentic shopping market?

The launch lands in a fast-moving market. More than 50% of global consumers have used AI to buy goods within the past three months, according to McKinsey, the consulting firm. Competing tools already include Meta Platforms' Muse agent and Amazon's Alexa for Shopping, plus retailer-built assistants from Lowe's, Ulta Beauty and Macy's.

Adoption of branded assistants, however, lags general AI use. McKinsey found that 56% of consumers use AI chat or search tools such as Claude or OpenAI's ChatGPT, while only 27% gravitate to retailer-created AI shopping assistants — a gap J. Crew intends to close with styling depth.

How did the project originate?

The Style Advisor was not mandated from the C-suite. A J. Crew digital product designer conceptualized the tool and developed a working prototype before engineers joined the project — an outcome Schmelkin attributes to her push for 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," she 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."

Internally, J. Crew runs an AI fluency program that starts with basics and advances to vibe coding (using natural-language prompts to generate software). An internal AI lab named "Second Thread," initially limited to the tech team, now includes all corporate employees who discuss AI use cases and propose technology solutions. For four years, the retailer has also hosted a two-day tech summit featuring workshops, hackathons, guest speakers and vendor presentations — programming recently opened beyond the tech team. Employees are encouraged to use enterprise AI tools from Anthropic and OpenAI.