Shop This Look
I Let ChatGPT Dress Me for a Week—Here’s What Happened
After much hesitation, I finally put ChatGPT’s styling skills to the test.
February 16th, 2023 was a day that started out like any other. I slipped on my favorite WFH sweater, sat down with my morning coffee, and clicked into the New York Times newsletter sitting in my inbox. But as soon as I scrolled, what had been a perfectly pleasant morning became the first chapter in a days-long spiral of existential dread—all thanks to a little thing called generative AI.
The newsletter had spotlighted Microsoft’s newly announced Bing chatbot, which apparently has an alter ego named Sydney who might profess its love to you via aggressive accusations such as, “You’re married, but you don’t love your spouse. You’re married, but you love me.” This was just one among many interactions with LLMs (large language models) that have gone viral in the last month. Funny at face value. Terrifying in the context of job replacement and the proliferation of misinformation—hence my anxiety.
AI is not new by any means, but it’s started to feel very real to me recently. Between Sydney’s scheming ways, a Friday night viewing of M3GAN, and a friend’s confession that they’ve been using ChatGPT to craft emails, it appears that robots are moving up in the world—whether I like it or not. And that’s just the thing: AI is here to stay, so we better learn to embrace it.
While I personally refuse to write with the help of AI, I have started to open my mind to the idea that it can be a useful tool for some. Of course, because I work with clothing, I was also curious about its styling abilities. So last week, I opened ChatGPT for the very first time and typed out a brief prompt: “Put together seven Power Casual outfit formulas—one for each day of the week.”
At first glance, the results are impressive—unnerving, even. But once I actually started my experiment of getting dressed according to these formulas, one thing was clear: ChatGPT won’t be joining our styling team anytime soon. To be sure, its outfit formulas certainly work—but only because they’re basic outlines. It doesn’t recommend specific styles, nor can it rival human creativity (yet?). In other words, I had to rely heavily on my own styling skills, which was both incredibly comforting and also quite fun.
Scroll below to see what happened when I got dressed according to my seven ChatGPT-generated outfit formulas.
Want more M Dash?
Sign up for our weekly newsletter.
Monday: Blazer + Jeans + Statement Flats
This first outfit made me realize the limitations of ChatGPT. Sure, it could suggest a blazer and jeans, but both are wide-ranging categories. What about color, texture, proportion, and all the other elements that make for an artfully balanced ensemble? I had some work to do.
Following my usual getting-dressed process, I decided to start with one piece I had an itch to wear and let that serve as inspiration for the rest of my outfit. I own three O’Hara blazers, so the probability of selecting one of them was high. The plaid one was calling my name that day, so I layered that over one of my favorite T-shirts and balanced out my boxy-ish blazer with skinny jeans. For the statement flats, I craved a pop of color on that dreary Monday, so I whipped out a vibrant pick—and lipstick to match. Between the boyfriend blazer, skinny jeans, and red flats, ChatGPT had provided the starting point, but I had selected the specifics. ChatGPT was a resource; I was the stylist.
Tuesday: Sweater + Midi Skirt
I own two “midi” skirts, and neither are made from cotton or wool (ChatGPT’s recommendations), so I was forced to break the rules here. I wasn’t really in the mood to style my tiger print skirt, so this left me with my black silk slip skirt. Despite the sun outside, it was a blustery day, so cashmere was a must for the sweater. Since early spring weather is especially unpredictable in NYC, I chose the Cece sweater so I could adjust the zipper if the temperature rose throughout the day. To stick with my sleek, black-and-gray palette, I slipped on my favorite loafers and added some silver hoops for good measure.
Wednesday: Turtleneck + High-waisted Trousers
A turtleneck paired with high-waisted pants is one of my go-to combinations—chic, elongating, and comfortable. While pretty much all of my pants are high-waisted, I settled on the Better than Denim Milo jeans, which look polished and feel especially WFH-friendly, thanks to two-way-stretch Turkish cotton. While nearly any turtleneck works with these pants, the slightly cropped Arbus sweater really emphasizes a long silhouette. I would know—I have four of them. Finally, I fastened on a black belt and luxurious slippers to feel extra put-together for my busy day ahead.
Thursday: Denim Jacket + White Tee + Black Jeans
This outfit had the potential to lean a little casual when considering my jam-packed day of meetings. So to balance out my vintage oversized denim jacket with some Power Casual polish, I chose elevated versions of each essential: a smooth, well-cut Pima cotton T-shirt and the Better than Denim Archie jeans—opting for a kick-crop style rather than a skinny jean. This decision process highlighted my ability to handle subtle nuance and make detailed decisions in a way that AI currently cannot. For my shoes, I went the ankle boot route, and for a little embellishment, I added the Dora earrings and an on-trend black bag. Once at the office, I ditched the jacket and changed into my favorite desk sweater.
Friday: Leather Jacket + Printed Dress
Our founder and CEO, Sarah LaFleur, recently interviewed Chrissy Rutherford, who shared some insights about her personal style that really resonated with me—particularly those about mixing “masculine and feminine themes.” I haven’t explicitly thought about my style in these terms before, but this mix describes some of my favorite looks, so I was especially excited to try out this outfit formula. I started by selecting the dress, since I knew the rest of my outfit would come easily once I had a print to go on. Our lightweight washable silk lends itself to easy layering, so the Alesia dress in icon print was a natural choice. To give this flowy silhouette some definition, I paired it with the Nicky jacket, which features a slightly cropped cut that hits around your waist. The rest was easy: Zelda boots for the win.
Saturday: Oversized Sweater + Leggings
After a busy work week, I was craving a night out, so I was ready to get a little bit dressed up. At the same time, I was also thrilled to see that ChatGPT had a cold-weather-friendly outfit in store—the temperature had dropped. An oversized sweater and leggings could easily look like the antithesis of night-on-the-town, but luxe styles like the slightly relaxed McKenzie sweater and the vegan leather Harrington leggings achieve a rich, textured look. If you’re not much of a leggings person, go with the vegan leather Archie pants, as I did. For the finishing touch, I picked out some leopard-print shoes—ignoring ChatGPT’s advice to wear slip-on sneakers or ankle boots. And to really zhush it up, I wore a vintage coat that I scored in Minneapolis when I was home for the holidays. Another move ChatGPT could never predict: my drink order. Apparently sake martinis are a thing?
Sunday: Chunky Cardigan + Boyfriend Jeans
On Sunday, ChatGPT told me to take a blessed day of rest, and I happily obeyed. The radiators in my apartment were on full blast, so instead of a chunky cardigan, I reached for a lightweight, ultra-soft option instead. I don’t own any “boyfriend” jeans, so I put on my “dad” jeans—which, according to Google, are defined as having a similarly loose fit but with a high waist. As far as footwear, I personally prefer not to “lounge” in ankle boots or sneakers as ChatGPT suggested, so I slid on some plush slippers before settling into the couch with a new novel and a cup of mint tea. For the record, I thoroughly enjoyed my tech-free, lazy afternoon. ChatGPT could never.