Brick-and-mortar retail will use AI to get revenge on E-commerce. And whether it is a man’s suit, an insurance policy, or weekly groceries, anyone selling something in a physical setting should pay attention.

“Chaos often breeds life, when order breeds habit.”

— Henry Adams, The Education of Henry Adams

MIT Technology Review, in a piece produced in partnership with Infosys, published a story on how Macy’s is repositioning as an “AI-first” retailer. Their Ask Macy’s assistant acts like a personal stylist. It knows your purchase history, reads context, and curates recommendations conversationally rather than algorithmically.

This means Macy’s AI agent could ask you a series of questions to match different clothing outfits with the occasion and your specific personality. Send the shopping list to your phone so you can try it on immediately. The expertise of a professional stylist in a self-service setting.

That’s a real capability. E-commerce can’t do that.

And the argument beneath it is genuinely interesting: AI can give physical retailers a form of personalization that e-commerce has never delivered at scale.

Amazon knows your transaction history. But it doesn’t know you. And the best physical retail experiences, the kind that made department stores dominant for a century, were built on human intuition. A great sales associate could read the room, ask the right questions, and send you home with something you didn’t know you needed. E-commerce killed that because convenience won. But “convenient” and “personal” are not the same thing. AI might finally close that gap.

However, Amazon has been running personalization at scale since before Macy’s understood what that meant. Catching up to your disruptor is not a competitive advantage. It’s table stakes today.

The real change that raises eyebrows in the Macy’s story isn’t the technology. It’s their new AI-first operating philosophy. “AI-first isn’t about adding intelligence on top,” says Macy’s senior director of engineering Murali Murugan. “It’s about redesigning how decisions happen.” That distinction matters more than any single feature. Retailers, and any business really, that retrofit AI onto broken systems will get marginally better broken systems. Retailers who rebuild around it have a real shot.

IMO, most legacy retailers will retrofit AI onto broken systems and operations.

Are you building something new? Or just making the old thing slightly smarter.