I’ll admit it: ChatGPT is good at some things. If you want to vibe-code a project, decode a legal document, or spice up your resume, a chatbot may save you some effort.
But when it’s time to choose lapels or buttons for your bespoke suit jacket, maybe leave the chatbot on mute. Tailors and menswear experts are bursting their seams over a new wave of clients who are challenging their expertise with information they’re finding on ChatGPT.
“It actually occurred during an entire fitting,” a North Beach tailor told me. “Our colleague would suggest something” — say a peak lapel, or a patch pocket — “and then [the client] would put it into ChatGPT in real time, and wait for ChatGPT to either affirm or oppose the suggestion.”
The tailor, who asked not to be named to protect his client relationships, was at a loss for words at this AI effrontery. Why cough up thousands for a personal, real-world experience if you’re going to defer to artificial intelligence?
On one hand, the point of getting a custom suit is that you can customize it. If clients want to go against what the tailor recommends, that’s their right. On the other hand, tailors have spent years immersing themselves in the craft and tradition of menswear, and clients pay for their expert guidance. All that becomes moot when you treat AI like your personal Tom Ford.
Menswear hobbyist Derek Guy, who has more than a million X followers, said this use of AI doesn’t surprise him. There have always been people who second-guess and micromanage their tailors, he said. Now they just have a new technology.
“What you’ll often see is guys who will go to a tailor, they’re budget-conscious, and therefore they’ve loaded a lot of anxiety into this big purchase, and so they’re prone to dictating the process,” Guy said. “In the past, that might have happened because a guy saw a suit on David Beckham and wanted one exactly like it.”
But unlike the sartorial tyrants of the past, who ran over professionals’ suggestions because they wanted a replica of a suit they saw in a magazine, today’s AI-reliant clients don’t seem to have a desired product in mind. They just want to make sure they don’t break the rules.
That lack of imagination is what’s most annoying for some tailors. Zach Uttich, founder of high-end tailor shop BLVDier in Chicago, detailed his encounter with a ChatGPT-bound client in a LinkedIn post.
“The biggest issue I have is that he didn’t want to have an opinion,” Uttich wrote. “It’s becoming an issue for me in life. When someone simply, apathetically, doesn’t care.”
The client came in with his fiancée to commission a suit for his wedding, Uttich said. When given a choice between five styles of buttons for his custom shirt, he turned to the chatbot, which suggested mother-of-pearl. Uttich agreed with the suggestion, but the client’s instinct to ask AI confounded him.
“A) Why wouldn’t you have your own opinion? B) Why wouldn’t you ask your fiancée? And C) Why wouldn’t you ask the clothing people? We’re literally clothiers,” Uttich said.
The implicit disrespect bothered him, but the client’s missed opportunity to develop his taste frustrated the tailor even more. Uttich and Guy both said that most customers may not know about suit styles, or that each shop has a house style.
Guy offered an analogy: You and I are going out to dinner, and you want Chinese food. But when we sit down, you change your mind and ask the waiter to bringspaghetti and meatballs. If you don’t like the Chinese dish that comes out, does that mean it’s a bad restaurant? No! It means you went to the wrong place.
“Once you walk through a tailor’s doors, 90% of the outcome has already been determined,” Guy said.
The North Beach tailor said he’d been mulling over options for clients who want to let ChatGPT make their decisions; he might even make them sign a waiver: I will not get upset and demand my money back if my suit looks like shit.
In the meantime, he just hopes clients develop an idea of what they want before they come in — rather than relying on ChatGPT to give them some kind of objective right answer.
“A lot of people do crave rules, because then they can have a stance,” he said. “I don’t know how to proceed with that conversation if you’re trying to be right, versus just sharing with me what makes you feel good.”
Wondering what ChatGPT would tell me about my own fashion needs, I gave the bot my dimensions and said I wanted a custom suit. It recommended a slim suit with tapered, flat-front trousers. But what if my tailor recommended pleated trousers instead? The chatbot said that’s fine, too, and shows my tailor knows what he’s talking about. The bot even encouraged me to talk through the benefits of each option with the tailor and gave me questions I could ask. So far, so good.
Then I told ChatGPT my tailor had asked me why I was trusting an AI more than a professional with decades of hands-on experience. Is it rude to use a chatbot in a tailor shop?
“That’s a thoughtful question — and honestly, it shows a lot of self-awareness on your part,” the bot said in classic supplicating fashion. It provided some reasons my tailor might be frustrated: “tailoring is a craft,” and he might feel like I’m not “fully engaging with his expertise.”
The best practice, ChatGPT continued, is to use it before the appointment — not during.