Microsoft’s AI assistant just got a wardrobe. As of mid-September 2025, Copilot can now suggest complete outfits and let you purchase items directly within the chat interface, thanks to a partnership with fashion-tech platform Curated for You. If you’ve ever asked a search engine “what to wear to a beach wedding,” you now get answers you can shop.
What Copilot’s New Shopping Experience Actually Does
The update adds a visual, shoppable layer to certain lifestyle queries. When you ask Copilot something like “Outfit ideas for a business casual dinner” or “What should I pack for a trip to Italy in October,” the AI may respond with a curated carousel of fashion items—each a clickable product card with an image, brief description, and a “Shop Now” button. Tapping one takes you to the retailer’s site to complete the purchase or, in some cases, a Copilot-assisted checkout.
Right now, five retailers are on board: REVOLVE, Steve Madden, Tuckernuck, Rent the Runway, and Lulus. They span fast fashion, rental, and contemporary wear, giving the recommendations decent range. The feature is live in the Copilot web, mobile, and Windows experiences as of September 17, according to an announcement from Curated for You and covered by Digital Commerce 360.
Behind the scenes, Curated for You’s engine selects items based on the context you provide—event type, location, season, even the mood implied by your query. Unlike a simple keyword search on a store’s website, this approach tries to understand the “why” behind your ask. “We’re helping consumers discover fashion the way they actually think — based on plans, moods, and moments,” said Katy Aucoin, CEO of Curated for You. Microsoft’s Jennifer Myers, principal product manager for Shopping, called it “turning Copilot into a style companion that understands your life.”
Who Benefits — and How
For everyday users, the feature is a novelty with real utility. If you’re fashion-agnostic or short on time, getting a pre-curated set of options beats endless scrolling through e-commerce sites. The suggestions are not just ads; they’re meant to feel like advice from a (very algorithmic) stylist. “It’s not just shopping; it’s discovery that feels personal,” Aucoin noted.
Power users and early adopters will appreciate the contextual smarts. If you allow Copilot access to your calendar or location, it could theoretically recommend outfits for an upcoming event you have scheduled or provide weather-appropriate picks. That level of integration, however, turns up the privacy dial—more on that below.
IT pros and administrators should note that this feature is currently rolling out in consumer-facing Copilot (the free version tied to a Microsoft account). Enterprise and education accounts with Microsoft 365 Copilot likely won’t see these commerce features, as Microsoft typically keeps the work and personal experiences separate. But the lines can blur if employees use personal Copilot on work devices, so it’s worth awareness. Remind users to keep work and personal accounts separate to avoid accidental data mingling.
For retailers, this opens a new discovery channel. If you run an online clothing store, you might want to explore the Copilot Merchant Program—a set of APIs and tools Microsoft offers to get your product catalog into Copilot’s results. The program, along with Copilot Studio, lets you feed inventory, images, and metadata into the system. Early adopters like REVOLVE see it as a way to reach shoppers at the exact moment of inspiration. “Partnering with Curated for You and Microsoft allows us to seamlessly deliver on this goal — by showing her highly relevant product curations right when she’s planning her next moment,” said Divya Mathur, chief merchandising officer at Revolve.
The Privacy Trade-Off
Whenever an AI assistant starts recommending stuff you can buy, the question of how it knows what you like (and who else gets that information) becomes critical. Microsoft has clear privacy rules for Copilot in Microsoft 365: your work data isn’t used to train foundation models, and your prompts are handled within your organization’s compliance boundary. But the consumer Copilot—the one now pushing fashion—operates under a different set of policies, and Microsoft hasn’t yet published a detailed data-use disclosure for this commerce feature.
Here’s what we know: the Curated for You integration relies on the text of your prompt, plus any contextual signals you’ve consented to share. If you’ve given Copilot permission to access your location, it might factor that into outfit suggestions (lightweight clothes for a hot city, for example). Calendar integration could let it suggest attire for events. These are all optional—you can always keep prompts generic and avoid granting those permissions.
What’s not transparent: whether your shopping queries or click behavior are used to refine the recommendation engine, what data flows back to the retailers and Curated for You, and how long any interaction data is stored. Until Microsoft spells this out, treat Copilot’s fashion advice the way you’d treat any social media product recommendation: convenient, but data-hungry. You can use the feature while limiting exposure by sticking to broad, non-personalized questions and reviewing the privacy settings in your Microsoft account (go to account.microsoft.com/privacy). The industry expects clearer documentation as the feature matures.
How We Got Here: From Search Box to Fashion Advisor
Copilot’s pivot into shopping didn’t come out of nowhere. Since its launch as Bing Chat in early 2023, Microsoft has steadily layered on capabilities—image generation, music creation, trip planning—all aimed at making the assistant a daily companion, not just a work tool. Commerce is the logical next step. In 2024, Microsoft introduced Shopping experiences inside Copilot for product search, and the company quietly built infrastructure to onboard retailers through the Copilot Merchant Program and Copilot Studio.
Curated for You, founded by Katy Aucoin, specializes in lifemoment-based fashion discovery. It already powers personalized recommendations for other platforms, but the Copilot integration is its biggest stage yet. The announcement on September 17 marks the first time shoppable outfits have appeared in a general-purpose AI assistant from a major tech firm—something that competitors like Amazon’s Alexa and Google’s Gemini have toyed with but not broadly released in this form.
The trend is called conversational commerce, and it’s accelerating. Instead of typing “summer dresses” into a search bar, you say “I need a dress for a summer wedding in Tuscany,” and the AI does the rest. For Microsoft, it’s a way to keep users inside the Copilot ecosystem, turning moments of intent into transactions without bouncing to a dozen browser tabs.
What You Can Do Right Now
Try it out: open Copilot on the web (copilot.microsoft.com), in the Windows 11 sidebar, or via the mobile app. Type a fashion-related query. For best results, be specific about the occasion, climate, or style. Here are a few examples that worked in our testing:
- “What should a man wear to a beach wedding in September?”
- “Outfit ideas for a first date at a nice restaurant in winter”
- “What to pack for a week-long business trip to London in March”
You’ll see a mix of text advice and, when the system deems it relevant, a shoppable carousel. Note: not every query triggers commerce results—queries that are too vague or off-topic may just receive standard text answers.
If you’d rather not share any personal data, avoid connecting Copilot to your calendar or location, and keep your prompts fact-based. There’s no dedicated “don’t personalize my shopping results” toggle yet—that kind of granular control may arrive in a future update.
For retailers: if you want your products to appear in Copilot’s recommendations, start by joining the Copilot Merchant Program (details at Microsoft’s developer site) and ensure your product catalog has high-quality images, clean metadata, and is tagged for lifestyle scenarios. Curated for You acts as an intermediary, so you’ll likely need to work with them or a similar curation partner unless you build a direct integration via Copilot Studio.
What’s Next
The first iteration is limited to five brands and a handful of query types, but expect the catalog to grow fast. Microsoft has a track record of scaling features quickly once the plumbing is in place. Within months, we could see home goods, beauty products, and electronics follow fashion’s lead. Google’s Gemini and Amazon’s Rufus are pursuing similar paths, so Copilot’s shopping chops will be a key competitive front.
The bigger question is trust. Microsoft must prove that its recommendations are genuinely relevant, not just paid placements, and that user data stays safe. If the experience leads to high return rates, biased suggestions, or a feeling of being sold to, it could backfire. For now, it’s a promising experiment—and a clear sign that your AI assistant won’t just answer questions; it’ll dress you for the occasion.