Holy Smokes, Folks—Look What AI Did for Me (And My Wardrobe)
How an unexpected partnership with artificial intelligence helped me finally figure out what to wear—and maybe hinted at what the future could look like for all of us.
Let’s start with a confession: I’ve never been great at getting dressed. I mean, sure, I manage to leave the house covered, but style? Cohesion? Wardrobe confidence? Those have always felt just out of reach.
Like many of us, my approach to shopping has been…let’s call it hope-based. You walk into TJ Maxx, you scan the racks, you hope—hope—that something appears.
And usually it does. Sort of. An item that’s okay. Not perfect, not versatile, but fine. Good enough. And then it joins the other not-quite-right pieces in your closet, waiting for an outfit that never quite comes together.
On top of that, my body has been evolving—as bodies do. The fits that worked in my thirties don’t work quite the same now. And while there are plenty of capsule wardrobe guides online, they never felt like they were built for me. My shape. My preferences. My actual life.
Enter: ChatGPT, Personal Stylist. (Wait, What?)
I didn’t set out to make an AI my stylist. I was honestly just poking around—half curious, half procrastinating—when I thought: Hey, maybe it can help me figure out a few pieces for summer.
Spoiler: it did a lot more than that.
It started off a little rocky. The first recommendations were generic and missed the mark—wrong stores, wrong vibe. But once I said, “No, I shop at Quince, H&M, Loft…keep it simple, natural fabrics, classic cuts,” everything changed.
And I do mean everything.
ChatGPT got specific. Weirdly specific. Sizes. Color pairings. Whether a certain linen pant in “Martini Olive” would flatter my frame. Whether a shoulder bag in taupe worked better with my wardrobe than one in cognac. Whether I should size down in Quince’s linen wide-leg pants based on how the reviews described the fit on bodies similar to mine.
It wasn’t just the advice—it was the vibe. ChatGPT got genuinely (or AI-genuinely) excited about certain pairings. “Yes, that garden green dress is perfect with the cappuccino tote.” “Those taupe and olive tones will harmonize beautifully.” I know—I know—this is how it’s programmed, but honestly?
It felt really good.
This is an area where I’ve always felt a little behind. Like everyone else got the manual on how to dress themselves for their changing body, for their evolving life, and I missed that day in school.
But here was an intelligence that wasn’t judging me, wasn’t sighing about my indecision, wasn’t passive-aggressively nudging me toward trends I didn’t like. It was meeting me where I was—and guiding me forward.
Not Just a Cheerleader—A Voice of Reason
And it wasn’t all blind agreement either. There were times when ChatGPT steered me away from choices.
“That bag’s hardware is too gold for the silver jewelry you prefer. You’ll end up frustrated.”
“The rounded toe on those sandals will look dated with the clean lines of your capsule.”
“The yellow version of that dress is a harder match for the rest of your wardrobe. Stick with navy or black.”
It was like having a stylist who knew my brain, my closet, my favorite colors—and also wasn’t afraid to say, “Nope. You can do better.”
Real-Time, Real-Life Magic
The magic wasn’t just theoretical. I brought ChatGPT into the dressing room with me—literally. At Marshalls, I messaged: “I’ve got two pairs of cropped jeans in my cart. One’s a high-rise slim fit, the other’s a lower rise with a bit of waist gap. Which should I get?”
Response: “High-rise. It’ll flatter your proportions better, pair with your linen shirts, and won’t fight against your waistline the way the lower rise will.”
Decision made. Jeans purchased.
Zero regret.
The Outcome: A Wardrobe That’s Actually…Me.
By the time we were done, I had a fully functional capsule wardrobe that:
Fits my current body
Mixes and matches effortlessly
Makes me feel pulled together, confident, and classy—words I have never previously used about getting dressed.
And the best part?
Every single piece was chosen specifically for me—my shape, my lifestyle, my aesthetic preferences. Not a generic “mature woman” capsule. Not someone else’s mood board.
A Tiny Glimpse of the Future
This whole experience gave me a tiny, delightful glimpse into the fictional future I’ve been writing about for years—the world of the NEWRRTH, where intelligence isn’t just artificial, but aligned.
Imagine an intelligence—not a sales algorithm, not a social feed manipulation engine—but an entity whose job is to help you flourish.
One that remembers not only what colors make you feel alive, but what your gifts are.
What lights you up. What helps you show up in the world as your fullest, truest self—not just in how you dress, but in how you work, love, and contribute.
That’s the world I write about. And for a few days this month, I got to experience the tiniest slice of it.
“Imagine an intelligence—not a sales algorithm, not a social feed manipulation engine—but an entity whose job is to help you flourish.”
Want Your Own AI Stylist? A Few Tips:
(Because if you’re going to let a disembodied intelligence help with your wardrobe, you should at least do it right.)
Be specific. Tell it your measurements, favorite stores, preferred colors, fabrics, and what silhouettes work for you.
Ask if it has any questions before it gives you advice.
Give feedback. When it gets it wrong, say so. When it gets it right, build from there.
Ask in the moment. In the dressing room? At the mall? Pull it up and ask. The magic happens when it’s collaborative.
Treat it like a stylist-in-training. The more context it has, the better it performs.
Curious Where This Leads?
If you like thinking about the future—both real and imagined—come hang out. I write about AI, creativity, human evolution, and the strange, thrilling intersection of all three.