Macy's AI Shopping Assistant Drives 375 Percent Spending Increase — The Gemini-Powered 'Ask Macy's' Is Now Live for All Customers

Macy's launched "Ask Macy's," an AI-powered shopping assistant built on Google's Gemini platform, across all its digital properties in late March 2026. The retailer tested the tool with roughly half of its website visitors over several weeks, and the results were striking: customers who engaged with the chatbot spent approximately 4.75 times more than those who did not. Bloomberg first reported the spending data on March 26. Fortune, PYMNTS, and TheStreet subsequently covered the rollout and its implications for the broader retail industry.

How It Works

The interface is conversational. Macy's prompts users to interact "like you would a store colleague," with suggested queries including "I need shoes for a special occasion," "Help me find a gift," and "I'm looking to refresh my bedroom."

Two features have driven the highest engagement. "Complete the Look" recommends shoes, belts, accessories, and other items to match an outfit a customer is already considering. Virtual try-on lets shoppers see how clothing looks on a model with a similar body type before purchasing.

The system did not ship in its current form. Thousands of Macy's employees contributed to iterative refinement before the public launch. Early versions produced mechanical, list-style responses. The team adjusted the AI to surface top brands in dress recommendations, account for regional weather differences when suggesting seasonal clothing, and shift toward conversational prompts — asking "Do you prefer bright colors or calm colors?" rather than presenting a grid of options. Store associates have begun using similar AI capabilities to assist in-person customers, extending the technology beyond the website.

The 4.75x Number — What It Means

The 375 percent spending increase reflects higher basket sizes and more confident purchases, not necessarily more visits. "Complete the Look" recommendations naturally increase average order value — a customer shopping for a suit gets prompted with shoes, belts, and ties that coordinate with their selection.

The question is whether this represents genuine value creation — customers finding products they actually want — or persuasion engineering, where AI-optimized sequencing increases basket size regardless of whether the customer needed the additions. The honest answer is probably both. A well-matched belt recommendation saves the customer a separate shopping trip. A fifth accessory suggestion after four accepted recommendations is closer to momentum-based upselling.

The broader industry is moving in the same direction. PwC data indicates approximately 40 percent of the top 20 US retailers by revenue have now deployed some form of AI shopping assistant, with most launches concentrated from mid-2025 onward. Ali Perhman, PwC's US consumer markets leader, drew a distinction between current implementations and earlier chatbot generations: "Effective AI is closer to a personal shopping agent that understands product composition and customer tastes, rather than just a chatbot." Entrepreneur reported on the wider trend of retailers racing to deploy similar tools before consumers shift their discovery habits to third-party AI platforms.

The Competitive Context

Macy's AI launch is as defensive as it is offensive. The retailer — and every major US department store — faces a specific fear: consumers bypassing retail websites entirely, using ChatGPT, Perplexity, or Google's AI Mode for product discovery instead.

That fear has a factual basis. OpenAI's ChatGPT recently launched conversational ads through a partnership with Smartly. Google's AI Mode now includes agentic booking and shopping capabilities that let users complete purchases without leaving the search interface. The platforms consumers use for discovery are increasingly the same platforms that complete the transaction. A retailer without its own AI assistant risks becoming invisible in that flow.

Macy's timing is notable. The company reported net sales decreased 2.4 percent in fiscal 2025, but returned to comparable sales growth of 1.5 percent. It posted four consecutive quarters beating analyst estimates. In fiscal Q4 2026, Macy's beat guidance with adjusted diluted EPS of $1.67, exceeding the high end of its range by $0.12. Bloomingdale's, the company's luxury banner, posted its best holiday comparable sales result on record — 9.9 percent growth in Q4. The AI assistant is arriving at what may be an inflection point in Macy's decade-long turnaround effort, giving the company a reason to invest aggressively in a technology that keeps shoppers engaged on its own properties rather than discovering products elsewhere.

Mubboo's Take

A 375 percent spending increase is a number that will get every retailer's attention. But the metric worth watching is not how much more customers spend — it is whether they return fewer items. AI-assisted shopping that increases basket size through intelligent recommendations is genuinely valuable. AI-assisted shopping that increases basket size through persuasion optimization may just shift the returns problem rather than solve it.

For comparison platforms, the Macy's result illustrates a broader shift: retailers are building their own AI advisors to keep consumers from leaving their sites. When the store itself becomes the advisor, the role of external comparison shifts from "help me find where to buy" to "help me decide whether the AI's recommendation is actually the best option." That is a harder question to answer — and a more valuable one.

Sources: Bloomberg (March 26, 2026), Fortune (March 27, 2026), PYMNTS (March 26, 2026), TheStreet (April 1, 2026), Entrepreneur (March 30, 2026), PwC.