Why Fashion’s Biggest Brands Are Betting on Daydream’s “Shop by Chat” AI Assistant

By
Jeanel Alvarado
Jeanel Alvarado is a marketer and retail strategist, leveraging 15+ years of cross-disciplinary expertise in retail, e-commerce, technology, consumer and shopping trends. She is the former...
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Why Fashion’s Biggest Brands Are Betting on Daydream’s “Shop by Chat” AI Revolution

In June 2025, former Stitch Fix COO Julie Bornstein introduced the e-commerce world to Daydream, a chat-based AI fashion shopping assistant designed to eliminate the endless scrolling, filter frustration, and decision fatigue that plague online fashion discovery. Powered by $50 million in seed funding from Forerunner Ventures, Index Ventures, GV (Google Ventures), and True Ventures, Daydream debuted with partnerships spanning from Nike and Alo Yoga to luxury leaders like Khaite, Casablanca, and cult labels including Dôen and LoveShackFancy.

How Does Daydream Work?

  • Conversational Fashion Search: Users interact with Daydream’s proprietary chat engine, describing what they want in plain language (I want a floral midi for a summer wedding or show me white sneakers that aren’t Adidas). They can also upload inspiration images, like influencer posts or Pinterest pins, and the AI finds precise or similar options across its global partner catalog.
  • Context-Aware Personalization: Every conversation refines a real-time Style Passport that remembers preferences for color, fit, favorite brands, budget, and even mood or event context, learning and evolving with every purchase or scroll.
  • Style, Not Search Bars: As Bornstein explains, “Online shopping today is completely overwhelming and time consuming. Traditional search falls short in fashion because it doesn’t understand the nuances of personal taste”.

Behind the Scenes: Who Built Daydream and Why?

  • Leadership and Expertise: Co-founded by Julie Bornstein (former Nordstrom.com, Sephora digital lead, Stitch Fix COO, founder of The Yes), Lisa Yamner Green (Chief Brands Officer), Dan Cary (Chief Product Officer), Richard Kim (Chief Strategy Officer), and Maria Belousova (CTO)—all with stints at Google, Pinterest, Amazon, Meta, Microsoft, and Farfetch.
  • Purpose-Built AI: CTO Maria Belousova clarifies, “We purpose-built Daydream’s AI engine specifically for fashion, embedding deep expertise in product details, brand insights, social events, and current trends directly into its core. By thoughtfully integrating nuanced understandings of style, fit, fabric, and individual preferences, our engine enables conversations that feel natural and serendipitous, delivering personalized fashion discovery experiences uniquely tailored to each user.”

Why Is Discovery Broken in Fashion—and Can AI Fix It?

For years, retail experts have pointed out that search in fashion has never been solved. This has real-world costs:

  • Billions Lost to Returns: Bad fit and uninspired discovery lead to staggeringly high returns—often over 30% for online fashion—which results in wasted logistics and environmental harm.
  • Overwhelm and Missed Sales: Users struggle to find anything in massive catalogs, abandoning sites before buying.
  • Stale Recommendations: Most platforms provide repetitive results, reinforcing sameness rather than guiding style evolution.

What Sets Daydream Apart?

  • Largest Curated Catalog: Over 8,000 global brands, both mainstream and indie, across price points, occasions, and styles.
  • Brand Opt-In: Labels like Nike, Khaite, Net-a-Porter, Markarian, MyTheresa, Uniqlo, Mejuri, Cult Mia, and more supply real-time, full-catalog inventory feeds.
  • Chat-to-Shop: A conversation-first approach, not retrofitted onto old search engines.
  • AI and AR Try-On: Virtual try-ons using augmented reality allow users to visualize fit and style, slashing return rates while elevating confidence.
  • Sustainability Signals: The next gen of the platform will highlight eco-friendly products and brands, nudging shoppers toward more responsible choices.

Industry Reactions and Future Implications

  • “Search in fashion has never been solved. It’s about discovery and personalization,” says CTO Maria Belousova.
  • Fashion experts call Daydream’s debut the most promising agentic AI retail launch so far, merging the ease of texting a stylist with the precision of a luxury boutique’s personal shopping floor.
  • Daydream is expected to spark a wave of innovation, pushing legacy retailers and rivals to rethink how discovery, advice, and purchase pathways are interwoven.

The Platform as a Solution

Daydream isn’t just another AI overlay. With its conversational, visually fluent shopping experience, founder-led domain expertise, and vast global brand partnerships, it’s making online fashion discovery less of a chaotic slog and more like magic, connection, and genuine style guidance.

As Bornstein affirms, our vision is for Daydream to become the smartest destination for fashion information, advice, and product discovery on the web.

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Jeanel Alvarado is a marketer and retail strategist, leveraging 15+ years of cross-disciplinary expertise in retail, e-commerce, technology, consumer and shopping trends. She is the former Senior Managing Director of the School of Retailing at the University of Alberta. Jeanel’s insights appear in Nasdaq, Entrepreneur, Fortune, TIME, and the US Chamber of Commerce, among others, with recurring commentary on top retailers and brands for financial markets, consumer insights, shopping trends, tech Innovation, and the luxury sector.