I Asked an AI Shopping App for the Best Winter Boots—Here Are 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, such as 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 I'm curious to see what Daydream will suggest.

Below, find my prompts followed by Daydream's responses. You'll notice the AI chat asks 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).

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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.

Response: These options offer a sleek, neutral palette with practical details that suit winter styling and straight-leg fits. Would you prefer something with a chunkier sole for added edge or a more streamlined, classic silhouette?

My Prompt: I prefer a classic silhouette.

Response: These boots lean into classic shapes and quality materials, fitting well with your preference for a timeless silhouette. Would you want to focus on taller shafts for more coverage or something mid-calf that pairs easily with straight-leg pants?

I decided to clarify my prompt thanks to Daydream's follow-up questioning because the first round of products didn't precisely match my taste. Second time around, I was pleased with the winter boot options. Find my top three below.

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Trendy Barrel-Leg

My Prompt: I'm looking for a pair of new barrel-leg jeans. Could you suggest a few?

Response: These options capture the barrel-leg silhouette with a mix of cropped and full-length styles, plus variations in rise and detailing. Would you prefer to focus on a particular wash, fit, or length to narrow down the vibe?

I spent some time scrolling through the product suggestions, since many were already out of stock or soon to be. So, I recommend checking on stock before you go all in. These AG Hattie Barrel-Leg Denim Jeans, $265, were a standout, plus they are available in sizes 23 to 31.

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Best Winter Boots to Wear With Barrel-Leg Jeans

My Prompt: I'd also like to find a pair of boots. Can you recommend some boots to wear with barrel-leg jeans?

Response: These boot options offer a chic blend of modern style and practical design to perfectly complement barrel-leg jeans. What is your comfort zone price-wise for this search?

My Prompt: $150 $300.

Response: These boot selections offer a chic and polished aesthetic within your desired price range to beautifully complement barrel-leg jeans. What color would you like me to focus on?

Lots of chic boots to choose from, but ultimately, these three Daydream suggested were my top contenders. Scroll on to shop the best winter boots to wear with barrel-leg jeans.

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Luxe-Looking Leopard

My Prompt: Leopard-print jeans are so chic. Could you recommend a few pairs?

Response: These options possess the chic vibe you're going for, with versatile cuts that feel very now. How would you describe the formality of your event?

Animal-print jeans are a big hit with the fashion crowd lately. I suspect their popularity will only rise come 2026. The first pair Daydream recommended just so happened to be the exact pair I've had my eye on: the Charlee Low Rise Straight Leg Jeans from Reformation, $198. Curious about what winter boots look best with animal-print jeans? Don't worry—I've asked Daydream. Scroll on to see what it recommends.

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Best Winter Boots to Wear With Animal-Print Jeans

My Prompt: Could you share some cute boot options that would go with animal-print jeans?

Response: These boots seem like they would add a fantastic, playful touch to animal-print jeans. What is your comfort zone price-wise for this search?

No need to refine the search because I already spotted three of the chicest boots to wear with animal-print jeans. Including a Zebra option, burgundy hue, and matching leopard print heeled boots.

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Fitted Flare

My Prompt: I'm looking for a new pair of flare jeans. Could you please recommend a few in stock?

Response: These flare jeans offer a flattering, gradual widening from the knee with options in classic denim washes and a mix of mid to high rises. Would you prefer a more vintage-inspired look or something with a modern edge, like frayed hems or distressing?

After browsing Daydream's picks, these Citizens of Humanity Kimberly High-Rise Flared Jeans, $260, had my name written all over them. While they feel retro, the pleated denim blends modern and classic.

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Best Winter Boots to Wear With Flare Jeans

My Prompt: I'm looking for a new pair of boots to wear with my flare jeans. Can you please recommend some boots?

Response: These boots present a polished and sophisticated look well-suited to your flare jeans, with options in a few universally chic neutral tones. Let me know what you think of these options.

Keep scrolling to see which three boots Daydream suggested would look best with a pair of flare jeans, specifically the ones above.

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Relaxed Low-Rise

My Prompt: I'm looking for a new pair of low-rise loose jeans. Could you suggest a few? I've been looking at a few Reformation jeans online.

Response: These lean more toward a straight-leg fit rather than the loose, baggy silhouette you're after. Would you like me to widen the search to include more relaxed or oversize cuts beyond straight legs?

I found it helpful to clarify where you like to shop, so Daydream can better understand your preferences and taste and curate products to your liking.

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Best Winter Boots to Wear With Low-Rise Baggy Jeans

My Prompt: I'd like to buy a new pair of boots to go with the low-rise baggy jeans. Do you have a few you could suggest?

Response: These options offer a nice mix of relaxed, edgy, and slightly retro styles that could pair well with low-rise baggy jeans. Would you prefer something more rugged and chunky, or something with a bit of a softer, vintage vibe?

I appreciate the edgy boots paired with a relaxed pair of jeans. Truly matches the vibe. Check out these three cool boots, best worn with low-rise, baggy denim this winter.

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