Magazines, blogs and makeover shows have been dictating our wardrobes for decades. Who hasn’t rolled their eyes at Cosmo columns insisting horizontal stripes will make you look wider, or hostile rules chastising anyone who dared mix black and navy? But while, in the past, style formation relied on discovery and friction – from the jacket you swiped from your dad’s closet to decoding some inscrutable editor’s reaction on the front row – fashion advice today is turning increasingly algorithmic.

Picture this. Your long-distance, low-commitment, casual pretend boyfriend is in town. You’re gearing up for the most romantic weekend of your life, but then, the dreaded question hits: What do I wear? With all avenues exhausted, you turn to that omnipresent oracle – ChatGPT. “Give me a chic but sexy date-night outfit that’s budget-friendly but still makes me look expensive,” you plead.

We don’t need to look far to find a community of fashion enthusiasts who are doing exactly this; TikTok alone will provides hundreds of examples. One woman discovered she was a “Pirate-Gypsy meets Desert Muse meets 2000s bohemian goddess” after letting ChatGPT analyse her Pinterest boards. Another user happily admits to using ChatGPT as their personal stylist, and gives others suggestions on what prompts to use. A third person uploads images of every single item of clothing in their wardrobe, then lets ChatGPT do the thinking. “I already pay for my AI subscription, so why would I also pay a stylist?” they write.

At first, it seems like a shortcut to salvation, a lower-effort way to keep up with an increasingly demanding fashion culture. But when both you and I get the same output from the same prompt, you start to wonder: does that effortlessness come at a price? The social media echo chamber is already dishing out formulaic aesthetics down to the last accessory, from gorpcore to coquettecore to mob wife. Trained on these pre-packaged personas, AI has no choice but to serve up one of the handful of cookie-cutter options it already knows.

So beyond panic-prompting an outfit for your cousin’s destination wedding, who actually benefits from AI stylists and the flattened culture they create? As online shopping continues to replace in-person retail – especially amid declining sales and a luxury slowdown – AI is increasingly positioned as a key tool for delivering a successful customer experience. It translates the cues and courtesies of the retailer into interface, with many fashion brands already rushing to tap in.

Ralph Lauren, for example, is betting on its late-2025 launch, Ask Ralph. Modelled on Lauren himself and functioning like a brand-specific 'For You' page, this AI tool aims to mirror the experience of speaking to a stylist, using natural language,  asking follow-up questions to refine its suggestions, and offering both individual items and entire outfits which it predicts its users are most likely to buy. ASOS on the other hand, has taken a more traditional approach. Its stylist tool likewise delivers personalised recommendations drawn from its multi-brand catalogue, but without the ‘For You’ page feel or chatty prompts.

“Even if it becomes harder to visually distinguish over time, I don’t believe that something created by a computer can connect with people on the same emotional level”

Despite these innovations across platforms, many users continue to turn to ChatGPT for fashion guidance, as evidenced by fashion-advice prompt videos that regularly attract tens of thousands of views. But given OpenAI’s recent collaboration with shopping conglomerate Shopify, which will allow merchants to sell directly through ChatGPT, a question arises: when an ostensibly neutral, all-knowing framework such as ChatGPT is rewired for commerce, does it risk masquerading sales pitches as impartial advice? The AI stylist is no longer a 24-hour helpful Samaritan, but a sleek, self-contained business model with a friendly interface, optimised to encourage more purchases. 

Why do people turn to AI stylists in the first place? In an increasingly demanding fashion sphere, AI can act as a safety blanket, reassuring you that your outfits are not terrible. But by design it avoids risk, stripping away the serendipitous magic of style formation. Would fashion subcultures even exist without risk? Without the spikes in punk, the studs of emo, or the white face paint of goth? After all, style is not a ‘problem’ that needs to be solved.

As stylist Jeanna Krichel sees it, we can't be afraid of progress: "You have to find your own way to move with it, surf the wave and make sure you don’t drown.” But at the same time, she doesn't believe that AI will ever reach the same heights as human expression. “We are human beings with soul, history, emotions and experiences. Even if it becomes harder to visually distinguish over time as the technology evolves, I don’t believe that something created by a computer can connect with people on the same emotional level,” she says. “We ultimately connect with the soul, the story, and the emotional core behind style.”

Developing a sense of style once took years of getting down and dirty, trawling through thrift archives to curate the perfect amalgam of your own experience. Now it comes at the tap of a finger, stripped of all lore and context. Ungated access to conformist style advice, presented as neutral fact, risks erasing the necessary cringe phase – our wardrobes wouldn't be what they are today without a few embarrassing outfits along the way. Fashion is a realm built on human friction, ambiguity, and excess, but AI doesn't encourage any of that. You will never discover that would-be-favourite, risky purchase again if the all-knowing algorithm decides it “doesn’t suit you.”

According to Emilio Ferrara, a professor at the University of Southern California who specialises in artificial intelligence, there is no doubt that AI is going to flatten culture. “Yes, especially when everyone buys the same ‘future’,” he says. "If brands use the same models, trained on the same data, chasing the same goals, you get convergence. Safer palettes, familiar silhouettes, fewer risks, and faster trend exhaustion.”

AI styling has real upsides: by allowing people to nail the perfect fit and minimise closet catastrophes, virtual try-ons and hyper-realistic visualisations could slash returns and reduce waste. But the flattened taste that these AI stylists produce is hugely profitable for brands. It means fewer stock-keeping units to manage, accelerated trend cycles, and less willingness to take a risk on experimental collections, all of which serves to line their pockets. The ultimate function of AI styling tools is to streamline their company’s operations, not help you to dress better.

We already know AI can sell you a t-shirt in your exact size, favourite colour, or for a predicted mood. It feels omniscient, like someone finally doing the thinking for you. But if we outsource our taste entirely, we might as well stop bothering to learn/ give up on learning about fashion. As AI stylists are positioned as the next frontier of shopping in 2026, this feels like a moment of choice rather than inevitability. Style has never come from having fewer decisions. It comes from making the wrong ones, publicly and repeatedly, and learning from them. You do not need AI to predict which shade of navy goes with burgundy when you can just try it on. Style is like a muscle you build, and like any muscle, outsourcing the work only weakens it. [it weakens/ atrophies when you don't use it]?