I Asked an AI Shopping App For the Best Winter Boots—Here’s 15 Pairs It Told Me to Style With Jeans

While I wouldn't say AI can replicate the intuitive aspect of shopping or the intrinsic elements of a human's identity, style, or fashion sense, I am intrigued by how new technologies focused on fashion can help curate results that inspire. Daydream, a chat-based AI-powered shopping platform, recently launched an iPhone app. Built to redefine online shopping, Daydream engages with users to provide a tailored shopping experience.

"We're building an intelligent layer of the world of fashion. One that understands taste, context, and individuality," said Daydream Founder and CEO Julie Bornstein in a press release. Users can search, converse, and shop via screenshots. The platform pulls products across a wide range of prices and categories from over 10,000 brands—Reformation, Revolve, Nordstrom, Saks Fifth Avenue, Madewell, J.Crew, to name a few.

With winter fashion in full effect, I couldn't think of a better way to try Daydream's capabilities than to find the best winter boots to pair with this season's top jean trends. As a shopping editor, I browse hundreds of product listings a day, and I know a standout fashion find when I see one, so it's safe to say, I'm curious to see what Daydream will suggest.

Below, find my prompts followed by Daydream's responses. You'll notice the AI chat ask for help refining the search (e.g., color, price, fit). The goal here is to better the curation to your taste. One thing I appreciate about the open layout of the product recommendations is that ultimately, you get the last say. Scroll down to shop the best winter boots to pair with jeans, recommended by Daydream AI.

'90s Slim-Straight

My Prompt: I'd like to buy a new pair of straight-leg jeans. I usually shop at Banana Republic, Madewell, and J.Crew.

Response: These straight-leg jeans offer a clean, classic fit with a nod to vintage denim, which aligns well with your usual brands. Would you prefer a version with any special details like raw hems or a particular wash to refine the search?

I was intrigued by the many chic straight-leg jeans Daydream offered. My pick? The Banana Republic's High-Rise 90s Straight Jean, $120.

Shop the Jeans

Banana Republic

High-Rise 90s Straight Jean

Best Winter Boots To Wear With Straight-Leg Jeans

My Prompt: I'd like to wear straight-leg boots with a pair of boots in the winter. Could you recommend a few boots that would look cute? My budget is $150-$300.