I let ChatGPT dress me

Spoiler alert: Stylists need not worry. At all.

Sure sure there’s all the talk about ChatGPT - will it replace copywriting, etc. etc. Just like when Love Is Blind contestants try to sing, I’ve looked away, hit mute and pretended it’s not happening. But then someone whose opinion I really value called and told me they used it (a paid, advanced version) to draft a work case. And was thrilled. “THIS IS A THING,” they said. “It.can.do.anything.”

Shit, did I actually have to start paying attention? I read the case, and I had to admit, it was scary-good, actually, if a teeny drop robotic. But what about an actual, life-or-death matter? Could ChatGPT dress me?

It’s easy enough to google the free version. I started with the simple “What should I wear today?”

And I wasn’t impressed. It didn’t like freedom to play, apparently.

But I guess how could I fault it for a classic creative move: Blame the brief. It spat back a bunch of completely unhelpful basics. An 8-year-old could have done better. (I know this because when I worked at Rue La La and my son Jack was 8, when we launched Kids, I had the employees’ kids dress us for a day, and although I refused to wear a swimsuit to work, I was inspired by Jack’s advanced print mixing.)

Anyway, ChatGPT put it back on me; they needed more information. So, fine. I added that I work for myself, like to walk, live in Miami, and my personal style is a mix of “heritage, approachability, Miami and modernity.”

Here’s the instruction I got. And then dressed to.

1. “a patterned sundress"

   What I wore: For starters I don’t own a sundress. Actually, I suddenly noticed that I haven’t been gravitating toward pattern at all. So I reached for one patterned long thing I own: a vintage Prada cotton coat. Which could function as a dress, I felt. I have strappy sandals, so easy enough. These are Tibi (currently a few pairs on sale!). I added a Marni belt from Cettire.

   What worked: I hadn’t thought to try this coat as a dress at all, and it reminded me that I like the piece. I liked this look in the photo.

   What didn’t: IRL this coat is tight on my ass (no judgement!), so it works open but I was really sausaged in here. That’s not ChatGPT’s fault; in fairness it’s pizza and margaritas-extra-salt’s fault. But again, no judgement! I could try open over a slip dress next time. But the exact prescription — the patterned sundress with a cardigan or denim jacket? That isn’t me AT ALL.

double belting effect via Leandra Medine here

2. “a modern jumpsuit”

   What I wore: No idea what a “modern” jumpsuit is. Isn’t a jumpsuit inherently modern? Even a vintage boiler suit consistently looks modern. And I don’t have a jumpsuit in “bold color or print” (see above re print, plus print in a jumpsuit just feels like a lot of print for me. Is that “modern” or “approachable,” ChatGPT?) So I picked the lighter of my two jumpsuits, i.e. the one that’s not black. It’s Philip Lim. (Mine is old; latest iteration here. Or check out this great option + price, an Etro one on Dora Maar.) Since I failed on the color front, I tried injecting color in the “statement earring” (also Philip Lim, bought used somewhere) and in a pink sweater at the waist. I added a flat as instructed. (Wait, does a loafer count as a flat? When I worked at M.Gemi I think I would have said no, that’s a loafer, but I suppose it’s both.) This is a Loro Piana loafer I got second hand. (You could too; I found a pair on ebay.) I also tried styling the jumpsuit the way that interested me — with my trusty Tibi heels, red socks + an old Barneys sweater.

   What worked: Overall I liked both looks, mine and the ChatGPT (ish) one. And I haven’t worn a jumpsuit in a while. So it was nice to break one out.

   What didn’t: Well I didn’t have a key item (the bold jumpsuit), but if I did, I think it would look very unlike me with the statement earring ChatGPT suggested. The loafer may have been cheating. Basically, the limitations of my own closet, not ChatGPT, made this proscribed outfit feel good to me.

Nothing could save this hideous “outfit” suggestion.

3. “a heritage inspired linen shirt”

   What I wore: Who on earth owns a “heritage-inspired linen shirt”? This was where I truly saw the ChatGPT’s Chat GPT-ishness showing. It’s like they just put my “heritage” and other adjectives in a blender and spit out a weak smoothie, where “heritage” was like an unblended frozen banana clump. When I use “heritage” as a style adjective, I mean elements with history, such as suiting or a loafer. Were they advocating some sort of cultural appropriation? I vaguely got that feeling. Like I was supposed to be putting on a guayabera? The closest thing to what they proscribed in my closet was a vintage RRL men’s shirt in super light chambray with the American flag on it, which I like to wear with opposite kinds of pieces with irony. While I own some cool Sperry x Boy Band of Outsiders trompe l'oeil boat shoes (more irony), they’re at my hub’s fam’s summer house. So I wore my Camper laceups, the next closest thing. And my new Palm Angels chino shorts. But wait, there was more. I had to read it again in disbelief. According to ChatGPT I was supposed to add a “fedora or Panama hat to complete the look.” Wtaf? I don’t know what a Panama hat is but I had that bad feeling again. I do have a straw fedora from a men’s hat shop in San Antonio that I wear to the pool.

   What worked: Nothing. Nothing at all. I mean, my new shorts are nice. That’s it.

   What didn’t: Offensive at worst, cornball at best. I looked fradiculous. It felt like wearing a horrible costume.

4. “a vibrant skirt…white or neutral blouse”

   What I wore: I was initially thrilled because I have lots of vibrant skirts and pants. I actually found more print! This Old Celine skirt bought second hand, which I was excited to rediscover. And then I got to the “white blouse” part. I have one “blouse” (what a word; more below) but it isn’t white and I’d sweat in it in Miami except on a cool night by the water. I used an Acne cotton shirt instead. Wedge sandals aren’t exactly at the top of my radar (ChatGPT isn’t getting on Anna Wintour’s Met Gala invite list anytime soon, even the table closest to the kitchen). But I did buy this one burgundy (looks like black but burgundy suede) Dior pair secondhand I saw long ago on Leandra Medine. And I have been gravitating to more delicate jewelry lately, but I grabbed some big bangles out of a drawer I hadn’t opened in a while and went to town.

   What worked: I would never pair this shoe with this outfit and I often struggle with “what shoe" (I think I’ve referenced here before a sentiment I’ve heard that the worst shoe often works. Or what Allison Bornstein calls the most unexpected shoe.) Just by limiting me with this callout to use a wedge, this brought me out of one of the reasons I don’t like print: You gravitate toward picking a color in the print for accessories, and then it can feel formulaic. I loved the maroon with this pattern instead of black. Also, it was fun to be reunited with the bangles I’ll always hold on to, even when not in my daily rotation, for just this reason. They felt new to me again. I really like the final look.

   What didn’t: No fashion person uses the word “blouse” - it’s like saying “slacks.” Again, ChatGPT your ChatGPT-ness is showing. Programmed by someone who called his grandpa for “fashion words.” Also, you asked me for information, and I told you I live in Miami, and no one wants to wear a “blouse” here in this heat. You could have easily taken me right where I went — a white cotton shirt. Classic heritage item. “Wedge sandals” sounds like a tall, cork thing. Not modern. I said “modern” was one of my words. Again, my own built-in closet limitations made this “me” — had I literally worn what ChatGPT suggested, I would not have looked like myself. Or many people in 2023, really.

here’s the thing …

The only elements that ChatGPT “got right” it actually got wrong, i.e. the changes I had to make to what it proscribed because I don’t even own the things it dictated, because they’re not my style. It worked only in the same way an IG “fashion challenge” does — by giving you parameters that force you to get creative with the pieces you have that are your style. That’s it. ChatGPT misses so much of the stuff I’ve been working so hard to tune into when it comes to fashion: the irony, the nostalgia, the beauty of “wrongness.” Personal style can’t be proscribed. Or programmed. Like, for example, I love Tibi. But when I see someone wearing it head-to-toe exactly they way it’s styled on the site, I don’t feel anything; they look cranked out on a cool assembly line. ChatGPT (if it weren’t stuck in 1950 or whatever) could proscribe an all-Tibi look that would be inherently modern, but even so, it can’t proscribe the things that an individual brings to it that make it feel like style. Emotion. Actual heritage (mixing old and new). The things that are so satisfying when they finally feel right, and maybe in part because they can’t be programmed. Because they have to be felt.