How I Tried to Glow Up with ChatGPT

And Learned That ChatGPT Has No Style

We have a long weekend here, and my body decided to get sick - just to make sure I truly get some rest. Between watching Big Little Lies and sleeping, I struck up a conversation with ChatGPT about - guess what - a glow-up.

It started innocently enough. I was wondering if I should do more for my skincare now that I’m 40 and wanted to understand which elements bring the highest ROI - facials, red light masks, retinol, vitamin C creams, and so on. Then I decided to send a few photos of myself- outfits, portraits, with and without makeup - and asked for advice.

As usual, ChatGPT was a bit timid at first, with the polite nonsense. But then I told it to go to the extreme - to tell me how to maximize my looks to the absolute limit - and see what it could come up with. I asked it to rank my potential versus my current situation, and here’s what it came up with.

Now, to be fair, while the scores were a bit ruthless, ChatGPT wasn’t harsh in its language. It praised me for my “natural elegance” and said I just needed to tweak a few things to maximize my potential.

I then dug deeper into all these areas, pushing it to give recommendations both with and without a budget. However, one thing I had to rein it in on was invasive procedures - I specifically asked for none. Otherwise, the highest-ROI recommendations started to look like this:

I then drilled down into skincare, which I later cross-checked with my dermatologist. To be fair, ChatGPT was pretty spot on and gave advice that largely aligned with my dermatologist’s recommendations. In a nutshell, the top priority is daily SPF - even indoors - along with a few active ingredients and moisturizing creams, while facials, massages, and even red light therapy are nice-to-have luxuries. Fair enough.

I then similarly drilled it on makeup and really liked its advice. It gave spot-on, practical suggestions that I tried - and found they actually worked. Nice.

Next, I asked ChatGPT about fitness. It suggested strength training to tone muscle and improve posture. It didn’t tell me to lose weight, even when I pushed it a bit, which I think is great (especially compared to #skinnytok - something I dread any 14-year-old scrolling onto). It recommended three more intense sessions per week rather than short daily workouts, as that’s more likely to yield visible results. It emphasized strength training over cardio, along with posture exercises. I didn’t press ChatGPT too much here - it all seemed obvious and made sense: just go to the gym. So far, so good.

That is, until we got to style. When I asked for style advice, it regurgitated the usual, bad internet tips: wrap dresses, emphasize the waist, tuck in your tops. I tried to steer it by uploading various outfit pieces, and somehow it managed to pick what I thought was the worst one as the best - because it showed off the waist the most. It also advised me to tuck in the top to emphasize the waist even more (ugh).

ChatGPT’s favorite outfit… definitely not mine!

I then explained that I like a modern, Tibi-inspired aesthetic and shared links to images of outfits I like. I asked it to generate outfit ideas with that aesthetic in mind—something modern and suitable for working from home. Here are the results it came up with. I mean no offense, but I could probably pull together an outfit with my eyes closed that would look better than the one in the middle. Anyway.

I didn’t lose hope and sent it another outfit featuring its favorite skirt, just to show that - really - it’s not a good look (sorry for cutting off my legs in the photo; I was wearing wool socks). This time, it agreed and concluded that the skirt would need to be more A-line to work for me. It then generated the second image.

Tonally, it wasn’t that bad - and yes, the more A-line version did look better. Still, the outfit felt a bit mature and slightly dated, so I asked it to create a more modern version. That’s when I got this green and pink beauty.

How on earth this is more modern, I have no idea. I gave feedback that the outfit was a disaster, and we finally settled on the last one. OK.

I then took a Tibi version of a somewhat similar look and asked it to visualize it on my frame. It was okay-ish, but nowhere near the relaxed vibe that Tibi is known for. I kept trying to get it to style the outfit with one size bigger clothes, but instead, it just kept making the frame look bigger and bigger - so I gave up.

So, ChatGPT as a style advisor? Not quite there yet for me, even though I really tried to communicate what I like. Style seems to be far more nuanced and less rule- or science-based than other areas of beauty or appearance. Even with a clearly defined aesthetic, ChatGPT struggled - often repeating the average of the bad advice that’s all over the internet. Then again, it might not be the recommendations themselves that are the issue, but rather the limitations of the image generator in capturing that nuance.

I’ll keep experimenting with ChatGPT and see if it can still play a role in my glow-up :) Let me know if you’ve been using AI to improve your style - and whether it’s worked for you!