Is AI Making Cher’s Closet a Reality?

Over the past year, ChatGPT has moonlighted as my therapist, personal assistant, and go-to source for decoding the drama between Blake Lively and Justin Baldoni. Recently, it added a new role to its résumé: personal stylist.

It started when I asked it to define my personal style based on my Instagram feed. Its response: “Barefoot luxury meets off-duty beauty editor, with a little bit of chaos mixed in.” In one sentence, it nailed me—so much so that I ended up down a full-blown AI styling rabbit hole.

“Give me an outfit idea that makes my legs look longer,” I typed. My robot BFF came back with a full look, featuring creamy high-waisted, wide-leg linen trousers; a cropped tank; an oversized, silky button-down; and strappy sandals. But it didn’t stop there: It explained why the outfit worked (a long, unbroken vertical line = legs for days), offered styling context (monochrome keeps things sleek, and slight tailoring adds polish), and even dropped bonus tips like trying slicked-back hair, emphasizing my posture, adding a long necklace, and swapping a crossbody bag for a clutch so I don’t break the silhouette. It also provided shoppable links for products, but I didn’t need them—I was able to re-create the perfect-for-me outfit formula using pieces that were already in my closet. 

Though ChatGPT’s outfit suggestions are (surprisingly) passable, the go-to chatbot is just the tip of the AI styling iceberg. New platforms are emerging that dig deeper into your closet, preferences, and habits to deliver styling advice that actually feels personal.

Beyond the Algorithm: AI That Gets You

A growing crop of tools is reshaping how we interact with our wardrobes—each tackling a different pain point, from shopping to dressing to smarter closet management. At a time when trend fatigue is real (looking at you, sardine girl summer) and #OOTD-fueled overconsumption is at an all-time high, these platforms are bringing emotional intelligence to the styling process, making it easier to dress like yourself, not everyone else. Think: the logic of a stylist, delivered instantly, and often for free. Nearly 30 years after Clueless hit screens, the dream of re-creating Cher’s iconic “smart” closet is finally inching toward reality.

While the app store is packed with tools that promise to transform your style with the help of AI, a few stand out for the way they bridge data with the emotional experience of getting dressed. Instead of spitting out algorithmic recommendations, they’re bringing human context to machine intelligence and ultimately, helping us feel better in our clothes.

Getty Images / Byrdie

AI That Speaks Your Style Language

On the shopping front, there’s Lily AI, which powers many of the tools you’re already using without you even realizing it. Lily enriches product listings with the type of language you actually use to search: Instead of filtering by “V-neck midi dresses,” you can search for “something flowy and flattering to wear to a summer wedding” and find exactly what you’re looking for. It’s the engine behind smarter site search, better recommendations, and more relevant ads across dozens of major retailers—including Bloomingdale’s, J.Crew, ThredUp, and many more. 

“We don’t live in a world anymore where you write a product title and description, publish it, and forget about it,” says Purva Gupta, the co-founder and CEO at Lily AI. “You have to constantly optimize for the world we live in now—and that means using the real language people use when they’re shopping.”

“The last two decades of ‘personalization’ have been pretty unintelligent,” she adds. “You buy a red dress and get shown more red dresses. You buy perfume and get more perfume. That’s not personalization. What’s happening now is a total shift—these new engines can actually follow instructions and understand what you want.”

AI That Shops Like Your Coolest Friend

While Lily focuses on enhancing the way products are labeled and found, Daydream zeroes in on how we talk about what we want, transforming that inner monologue into outfit recommendations that feel almost telepathic. 

The app takes a more conversational approach to combat the overwhelm so many of us feel when shopping online. The chat-based platform lets you describe what you want in plain language (“a cool outfit for a first date that doesn’t make me look try-hard”), asks thoughtful follow-up questions, and delivers hyper-specific recommendations pulled from a catalog of over two million products that have been curated with the help of professional stylists. In practice, it’s essentially like texting your most fashionable friend who happens to have AI superpowers. 

“Shopping online could be so much better than it actually is,” says cofounder Lisa Greenbaum. “No matter how much money you spend on a specific site, you still go back and they show you the same products they show your sister, your mom, and your daughter. They know enough about you that they shouldn’t have to do that anymore.”

Over time, Daydream starts to actually understand you. It gets to know your style, your budget, and your deal-breakers so it can deliver things you want to wear. Instead of wading through dozens of silhouettes you’d never even consider, the app just skips straight to the good stuff.

“Most personalization today is really shallow. It’s like: You bought this, so here’s more of it,” says Greenbaum. “Our vision is a shopping companion in your pocket—something that understands what you want and helps you get there, not just something that reacts to what you bought last.”

Illustration by Byrdie.

Getty / Byrdie

AI That Organizes Your Closet—and Your Life

And finally, there’s Whering, which is arguably the closest thing we’ve got to the Clueless closet IRL. The app lets you digitize your wardrobe, swipe through pieces Tinder-style to build outfits, plan looks using mood boards, and track the cost per wear of everything you own. It even helps you shop more intentionally by identifying what’s missing from your closet so you’re buying things you really need, not just adding more to your cart in pursuit of a dopamine hit.

“We’re not here to be your bossy AI stylist,” says founder Bianca Rangecroft. “We’re here to reduce friction, spark creativity, and make your closet work harder for you.”

That creative freedom is central to the app’s mission. Instead of telling you what to wear, Whering is designed to help you rewear what you own in new ways and explore your style on your own terms. “AI should never feel mechanical or prescriptive,” says Rangecroft. “It should support your creativity, not replace it.”

Whering also doubles as a styling community, where users can crowdsource outfit advice, browse public closets, and help others create looks in real time. “People want real connection,” she says. “They want to be surprised. Someone can come into your wardrobe and completely shift how you see a piece you’ve had for 10 years.”

That emphasis on reuse and human connection is baked into everything Whering does. “Soon, you’ll be able to one-click resell or donate an item you haven’t worn in a month, right from the app,” Rangecroft says. “It’s circularity made simple.” 

Ultimately, she adds, the platform’s mission is much bigger than getting dressed. “We want to build one wardrobe for the world.”

The Future of Fashion Bridges Robot Intelligence With Real People

Together, tools like Lily AI, DayDream, and Whering are forming a kind of AI fashion ecosystem—one designed to make shopping and styling feel less overwhelming and a whole lot more you. And in the process, they’re encouraging smarter consumption and creative expression.

“Our goal is to help people build closets that actually make sense for them,” says Greenbaum. “Dressing ‘well’ doesn’t mean dressing like your friend. Everyone has their own body type, coloring, and needs—it’s about dressing well for you. We’re trying to help people buy better, return less, and wear things more.”

This is just the beginning of a massive shift in how we get dressed, and more players are bound to enter the space in the not-so-distant future. But the ones that will stick are those championing a full-circle model, from discovery to daily use to resale. “The platforms that win will be the ones that serve the entire user journey and use data to understand what people actually want, not just push more product,” says Rangecroft.

Right now, that journey hinges on pairing human expertise with generative AI. At Daydream, professional stylists help curate the shopping experience and share insights from their own wardrobes. On Whering, users co-create outfits with strangers on the internet. Instead of just spitting out ideas based on an algorithm, these platforms invite real people into the process.

ChatGPT gave me a solid outfit, sure. But the future of styling isn’t about “good enough”—it’s about feeling better than ever when you’re getting dressed.

“AI doesn’t have to be scary,” says Greenbaum. “We’re using it to make life easier, not to replace people, just to support them.”