AI Models Are Pretty Decent Tutor-Stylists

How to develop taste using an unreliable but useful advisor

A classic way of figuring out if AI is a good fit for whatever use case you care to name is this thought experiment: “How comfortable would I be delegating this task to a 140 IQ savant who is also just a little bit schizophrenic and prone to, 10% of the time, just making some shit up?”

Anyway, there are a number of ways you can make use of ChatGPT or Claude or Gemini as your free-ish fashion advisor.

Ideation

I think most guys who aren’t otherwise conscientious about their style choices have one or two items in their wardrobe that they really like and wear at every opportunity.

A way you can select a style direction/Type Of Guy is checking: “which of these fashion directions does my selected article of clothing potentially vibe with?”

You can ask Claude or ChatGPT this, by the way. It’s trivial to upload a couple pictures of you wearing a thing and telling it “I want to build this specific item into an outfit, what fashion directions is it compatible with? And what kinds of outfit would it work in?”

Then it’ll give you a bunch of ideas and you can— and indeed should— have ChatGPT (or Gemini) draw one or all of them for you:

And then, you combine that with your own photos:

Pretty good!

This is a great way of running through lots of different ideas and seeing which ones you vibe with, without having to try on a shitload of clothes and figure out sizing and fit and whatever.

Note that it is, occasionally, buggy:

Excellent work, Gemini. No notes.

Anyway, a redo generally suffices for these situations:

It’s me! In some kind of bohemian outfit! Where did I get the bohemian outfit image, you ask? Midjourney. Slop in, slop out!

And thus, I can then feed that image back into gemini or chatgpt and ask it to find the relevant items online:

This… actually doesn’t do a very good job at locating specific garments matching the image. But it tries! (Actually, the core “problem” here is that Midjourney is pulling from the latent space of all clothes that could possibly ever exist, and the specific items it’s showing do not exist in any form anywhere in the world, and therefore OF COURSE ChatGPT will fail utterly at finding these for sale online.)

Visualization For Specific Garments

One can also use Gemini’s image creation functionality to create pictures of yourself wearing a specific item of clothing. (For whatever reason, Gemini is the only image model I’ve seen thus far that does a good job of reproducing specific people wearing different clothes or doing arbitrary things.)

which gets you:

One can also do this with sets of clothing (images from Amazon; I’ve been putting together an 1880s Victorian-era doctor outfit for a LARP I’m doing mid-December):

Of Course This Is An Approximation

AI models don’t know how big a shirt is relative to you or how it’s gonna fit. What they’re going to actually do is give you, more or less, an idea of “how would this shirt or whatever look on you IF IT FITS PERFECTLY” which is a hell of an “if.”

Nevertheless, it beats the hell out of ordering an outfit, looking at yourself in the mirror, and being like “eh, vibes are off.”

“How Does This Look?”

Fit and color is yet another place where you can lean on AI models. Here’s me asking GPT-4o (this is from a while back) about how it felt about a shirt’s fit:

Yes, it is too large.

AI models have only improved in their ability to do fit assessments, and I think that most of the time they do a pretty good job of telling you both how well something fits and— just as importantly— how it knows. Claude and ChatGPT and Gemini will all inform you that your shirt’s shoulders are too wide or that the buttons on your jacket are pulling or any of the other numerous things that go into your clothes fitting well.

AI Makes Visual Hallucinations With Great Frequency

Claude 3.5 Sonnet:

You will notice that I gave it an image with a chore coat, not a vest. (Interestingly, its callout that the chore coat is too big was accurate.)

Regardless, It Provides Consistent, Actionable Feedback

Let’s check GPT 5.1 Thinking:

As is traditional ChatGPT would like to glaze the hell out of me, though it arrives at some of the same recommendations as Claude above. ChatGPT, Claude and Gemini are all pretty united that I should be wearing tighter jeans than I am. (I am not interested in doing this, but I respect that the AI bots here are speaking truly of the current moment where people love skinny jeans on men for, like, reasons.)

I also appreciate that sometimes I can already tell something doesn’t quite look right, and all the current SOTA-ish models are able to pinpoint why in a way that feels satisfying and actionable to me.

AI Fashion Critiques Have Excellent Inter-Rater Reliability

The most common things that ChatGPT and Claude complain about in my outfits are:

(1) I prefer more relaxed fits on jeans than is currently considered “correct”; and

(2) I wear Hokas most of the time because I gotta save my knees for dancing. Hokas are definitely athleisure only and I intentionally choose colorways that try to blend with the rest of the outfit, but these always get called out as problematic no matter what AI model I’m making use of.

I’m pretty sure that they are in fact correct in this assessment; I have made the tradeoffs I’m comfortable with in this domain but the fact that these get consistently called out imply, crucially, that the AIs aren’t just glazing me mindlessly in other domains. Shaming me for my enormous, clown-shoe-like Hokas is a canary in the coal mine for “is this AI performing a useful service when I upload my photos for critique.”

Conclusion

When I was first starting to pay attention to the clothes I was wearing, I couldn’t tell if anything new looked good or not. Literally, I had no idea; my perceptions were dominated totally with how different it all looked.

The 140 IQ schizophrenic savant test holds up. Yes, Claude will sometimes hallucinate vests. Yes, the AI-generated outfits frequently don’t exist in any purchasable physical form. Even so, having something to bounce ideas off of is enormously useful because you start to see patterns in (1) what gets flagged as problematic by the AIs in IRL photographs and (2) what feels good or bad to you when you see yourself in what amounts to the best possible version of the clothes. You’ll develop vocabulary for fit and proportion. And crucially, you build up a reference library in your head of what works and what doesn’t, so you’re not starting from zero every time you look in the mirror.