I Asked ChatGPT for the Best 2026 Fashion Investments—Here's What It Got Totally Wrong

a woman wears a black coat
(Image credit: The Style Stalker)
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I have a love-hate relationship with AI chatbots. I appreciate when ChatGPT helps me understand the tax implications of selling a stock, plan a weekly budget, or convert grams of my dog's new kibble into cups. (Notice how all of my inquiries are math-related? Yeah, it's not a coincidence I became a fashion writer, not a computer scientist.) However, chatbots have frequently given me inaccurate answers, even ones that contradict what they told me just ten minutes prior!

For that reason, I was a bit skeptical to ask ChatGPT for its recommendations on 2026 fashion investments. As it turns out, I was right to be worried. The list was innocent enough, but as a veteran fashion editor with 15 years of experience, I quickly identified several flaws. Continue reading to learn more about my (mis)adventures in AI.

1. It Lacked Personality and Emotional Resonance

ChatGPT's list of investment recommendations included a tailored black blazer, a camel coat, simple sneakers, the perfect white T-shirt, basic straight-leg jeans, minimalist pumps, high-quality gold jewelry, and low-key sunglasses. Everything was devoid of personality and emotional resonance. (Yep, AI is artificially intelligent, alright.)

When ChatGPT explained why something was a good investment, it spewed predictable lines about versatility, cost per wear, and ease of use. Where's the fun in that? Where are the pieces that will make you feel more confident, trendier, cooler, sexier, richer, smarter, or more well-traveled? Purchases that will make you feel something. Anything! Where are the items that will garner compliments and raise questions? Well, for that kind of advice, you might want to rely on humans who are actually capable of feeling these things. After all, you're bound to tire of clothes you don't feel connected to.

a woman wears a furry coat

(Image credit: Stephanie Geddes)

2. It Wasn't Reflective of the Cultural Zeitgeist

ChatGPT's suggestions could have been written in 2006. I'm serious. The list didn't take into account anything currently happening in pop culture, art, film, finance, music, or literature. It didn't reflect TikTok algorithms, emerging street style scenes, fashion industry news, or award show red carpets. It didn't acknowledge the renewed interest in Carolyn Bessette Kennedy's minimalist '90s style thanks to a new TV show. ChatGPT didn't consider statistics on which brands are retaining their resale value on The RealReal right now. It didn't study Chanel's new creative director. Your friendly neighborhood fashion editor, however, keeps all of these things in mind (and so much more) when making shopping suggestions.

a woman wears a Birkin

(Image credit: The Style Stalker)

3. It Ignored Trend Fluency

A big blind spot in traditional fashion investment advice is the assumption that trends are fleeting distractions rather than tools for long-term strategy. Most guides write for people afraid of misstepping, but Who What Wear readers know cycles and understand which trends have staying power.

Investing in fashion for this particular audience isn’t about ignoring trends in favor of everything beige, businesslike, and banal. Certain pieces might feel too outside-the-box now, but trend-literate fashion people can recognize long-term potential. Ignoring this perspective is one reason why ChatGPT's list feels so stale.

a woman wears a gray cardigan

(Image credit: The Style Stalker)

And Now, Investments Recommended By a Sentient Human

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Erin Fitzpatrick
Erin Fitzpatrick
Associate Director, Fashion News

Erin got her start as a Who What Wear intern in 2011—back when the site only published a single story per day. (We have since increased that number twentyfold.) She graduated magna cum laude from USC and lives in Los Angeles. In college, she also interned at Refinery29, where she was promoted to editorial assistant and then assistant editor. After nearly three years at R29, she came back to WWW in 2015, where she is now the Associate Director of Fashion News. From the Oscars to the Met Gala, she leads the site's entire red carpet coverage strategy. She specializes in celebrity and fashion news but also enjoys writing travel features and runway reports. She frequently contributes to WWW's social accounts and has a sizable following on her personal TikTok.