Macy's AI Shopping Assistant Makes Customers Spend 4.75x More — And Every Major Retailer Is Watching

Macy's launched its "Ask Macy's" AI shopping assistant across all digital platforms on March 23, and the early numbers are striking. During several weeks of testing with roughly half of its website traffic, customers who used the chatbot spent approximately 4.75 times more than those who did not.

The assistant is powered by Google's Gemini platform and functions as a conversational shopping interface. Users describe what they are looking for — an outfit for a specific occasion, a gift within a budget, accessories to match existing items — and the system responds with curated product suggestions.

What Makes It Work

Two features are driving the strongest adoption. "Complete the Look" recommends shoes, belts, and accessories to complement a selected outfit — turning a single-item purchase into a multi-item basket. Virtual try-on lets customers see how items might look on them before buying.

The system was refined with input from thousands of Macy's employees before launch. Early versions were criticised for returning mechanical, list-style responses when asked broad questions like "What t-shirt should I buy for a 10-year-old?" The current version asks follow-up questions: "Do you want bright colours or something more muted?" — mimicking how a store associate would guide a customer.

Regional customisation was also added. The system adjusts recommendations based on local weather and climate, ensuring it does not suggest heavy coats to shoppers in Florida or summer dresses to shoppers in Minnesota in winter.

The Bigger Picture

Macy's is not alone. According to PwC, approximately 40% of the top 20 US retailers by revenue have now deployed some version of an AI-powered shopping assistant, with most launches occurring from mid-2025 onward. Amazon introduced "Buy For Me," an agentic tool that lets customers shop other retailers' websites without leaving the Amazon app. OpenAI embedded direct checkout from Target, Instacart, and DoorDash inside ChatGPT.

The race is driven by a defensive calculation. As consumers increasingly turn to external AI tools — ChatGPT, Perplexity, Google's AI Overviews — for product research and discovery, retailers risk losing the first interaction. If a shopper asks ChatGPT "What running shoes should I buy?" before visiting any retailer's website, the retailer has already lost control of the recommendation.

Max Magni, Macy's Chief Customer and Digital Officer, acknowledged the experimental nature of the technology: "Every retailer is trying to figure it out one step at a time. This is anybody's game. Nobody has cracked the code."

Mubboo's Take

The 4.75x number is impressive, but it needs context. This is early-adopter data from a self-selecting group — customers curious enough to try a new AI chatbot are likely already high-intent shoppers. The real test is whether the spending lift persists as novelty fades and as the tool reaches less engaged users.

What is genuinely significant is the mechanism. "Complete the Look" is essentially AI-powered cross-selling — the same thing a skilled store associate does when they say "That jacket would look great with these shoes." The difference is that an AI can do it for millions of customers simultaneously, with personalised recommendations based on browsing history, purchase data, and stated preferences.

For consumers, the question is whether these AI assistants are genuinely helping them find better products — or whether they are sophisticated upselling engines designed to increase basket size. The answer is probably both, and independent comparison platforms exist precisely to give consumers a second opinion before they click "buy."