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.
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.
(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.
And Now, Investments Recommended By a Sentient Human
Jimmy Choo
Eliot Slippers
J.Crew
Collection Embellished Shift Dress in Memory Satin
Zara
LEATHER MINI SHOPPER
Loulou de Saison
Jiha Shawl Collar Jacket
WARP+WEFT
Ase High Waist Straight-Leg Jeans
Stine Goya
Square Neckline Tailored Jacket
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