Inside AI’s $5 trillion quest to develop taste

The assignment is charming: I’ve been asked to moderate a panel in a garden in early summer. The problem is that it will require an outfit I don’t own and have no time to find. Easy enough, I think. I use AI every day to summarize transcripts, synthesize financial data, and draft emails. Surely I can outsource this. I open Chat GPT and ask it to find me a dress from my favorite label, Sézane, that’s appropriate for an outdoor professional event. It pulls dresses from the French brand’s catalog that are made of linen and crocheted—floaty, unstructured things that require a level of undergarment coordination I don’t want to think about. I clarify. It pivots. After several rounds of negotiation, it finally surfaces a red polka-dot dress I like. There are no links. I go to Google, search manually, and discover that the dress is from last season and available only in a size 2 on Poshmark. Twenty minutes after starting my search with ChatGPT, I give up. I head over to Sézane’s website and buy something the old-fashioned way. Artificial intelligence has, in the span of a few years, displaced coders, passed the bar exam, and written term papers for an entire cohort of college students. Yet, the technology that’s remaking civilization still can’t help me buy a dress. The retailers who crack this code are likely to own the next era of online shopping. When ChatGPT launched in 2022, becoming the fastest-adopted consumer technology in history, it lit a fuse. Behemoths like Amazon and Walmart, along with smaller players, raced to roll out AI-powered assistants to help customers find the right product from their catalogs. Soon startups like Daydream, Phia, and Remark were pulling in millions in venture capital funding to build AI shopping agents that could offer hyperpersonalized product recommendations. Over the past year, OpenAI, Google, and Anthropic have been working behind the scenes with the e-commerce infrastructure giants Shopify and Stripe to build essential retail plumbi