The AI Stylist Thinks I Have Plans Tonight
Ghosts of a Past Life in My Digital Closet
I used to treat the office bathroom like a backstage dressing room. In an era full of Refinery29 “day to night” advice pieces, I’d mastered the art of the quick change: I’d swap my Veja sneakers for a pair of YSL platforms I kept in my desk drawer rotation along with a silk scarf (could be worn as a top with my work trousers for an after-hours “office siren” vibe) and finish the look off with one of the many red lipsticks I’d have in a drawer, in a purse, in a laptop bag, etc. I could go from “responsible startup marketer” to “Lebanese Carrie Bradshaw” before anyone caught onto the fact that I was sneaking out thirty minutes early. A flourish of mascara, a quick hair tussle, and I headed to the train to meet friends for a basic bitch happy hour in a much trendier neighborhood. It’s just what “you” did.
Now, five and a half years after my most recent big city office job, a year and a week into motherhood, and eight months into marriage, the after-work dance looks a bit different. At my husband’s encouragement, I recently invested in a few pairs of J. Crew linen drawstring pants, a game-changer. Before that though, I’d wear some some combination of Athleta leggings, a baby tee, my beloved Everlane pull-on shorts, an oversized button-down, or big ole hoodie with nothing but a pair of hot pants underneath.
My unworn clothes whispered to me from my closet room, dresses elegantly draped on their clothing rack, sky high stilettos and granny heels both begging to be taken for a spin around the block. “Just one more gin gimlet with the girls, please,” they’d plead, longing to be dragged up and down piss-speckled subway steps just one more time. “I don’t live there anymore, I don’t have ‘girls’ here, we can’t do that anymore,” I would respond.
Pitiful.
In an effort to reclaim a bit of myself postpartum, I downloaded an AI-powered closet app called Alta. I’d convinced myself it was a practical move: digitize my wardrobe (I loved the process of documenting and categorizing everything), wear more of what I already owned, and reduce the mental load of getting dressed so that I could have more creative energy for the important things like writing a Substack and finishing the song I’ve been “getting done” fix six months now. I also really needed to master the art of “shopping my own closet.” Like most women, I love new clothes. I enjoy acquiring them and imagining the version of myself who might eventually, aspirationally, wear them.
“This top will be perfect for if I ever go to Harp & Crown with Rebecca again for an after-work drink.” (Doubt.)
“Tyler would like this sundress the next time we’re able to have a date night.” (Maybe in the fall, when it’s too cold for a sundress.)
“I probably have a work trip coming up eventually, I need this menswear blazer to force out my masculine side.” (I’m going to feel “too broad” in it and leave it thrown on the hotel bed.)
It’s vanity for sure, with a hefty dose of “my brain wants to gather berries all day and what is my TheRealReal cart if not a basket of berries?” and some Lacan thrown in for good measure. I’m not looking to impress anyone but myself, I want to see a version of myself reflected back at me that transcends the daily identity crisis.
Alta offered a tidy little promise: upload my wardrobe, get daily outfit suggestions tailored to the weather, my location, and even my “vibe.” Cycle through what I already own without having to think about it too much.
In typical “me” fashion, I pursued ease but got existential whiplash instead.
Immediately after the thrill of completing my closet inventory, I was met with a surrealist version of my life, laid out in neat little grids, shining a spotlight onto the the uncanny struggle between who I was and who I am. The weather was accurate. The outfits were technically plausible. But the occasions? Utterly delusional.
You see, in West Virginia, you don’t go out for after work drinks with the girls. There’s pretty much nowhere to do it. And even if you do, I do not, because I have no friends here. Given that context, imagine an AI’s confusion when it comes to spinning up OOTD suggestions for local occasions.
One morning, the app suggested I wear a pair of tapestry mules, a silk blouse, and a French-girl-chic wicker handbag for… foraging. Not much else to do around here, I suppose. And yes, foraging. As in mushrooms. As in crouching in the woods. A vision of bucolic chic pulled from someone’s #cottagecore Pinterest board and slapped onto my Tuesday, which in reality would look like Zoom calls with clients, a trip to Walmart, and a stroll around the track at a local park if I could finish everything I needed to do for the day.
Another day, it offered up a sculptural shoulder pad dress with knee-high boots—“perfect for dinner and drinks,” it claimed. Reader, I had no dinner plans. The closest restaurant in which that look would be acceptable is over an hour away and, with work schedules and baby, requires some logistical planning to pull it off.
It became clear: Alta wasn’t styling me—at least not the version of me who is actively occupying this body. She was dressing a projection, a specter of the past. She was building looks for the composite woman my closet claimed I was: busy, mysterious, possibly French, maybe a little sexy, always between one interesting thing and the next. Part socialite, part career woman. All free to do what she pleased.
My closet is full of that woman: Silk slip dresses, tailored pantsuits, architectural heels, bags too small to carry anything practical, like wipes or protein cookies or a deodorant bar. Alta isn’t wrong. She’s just working off outdated intel.
It’s a strange feeling to be ghostwritten by your past self, but I’m not exactly mourning her. Life now is quieter, but it’s not lesser. It’s just different now, a little transient, and very difficult to style. The challenge now is to dress the woman I am, without pretending the woman I was never existed.
The hardest part of getting dressed now isn’t about fit or flattery, it’s about the integration of these two seemingly disparate selves. Not every day, but often enough, I want my clothes to affirm something about who I am becoming. I want them to say: She’s still in there. She still gets dressed on purpose and she looks good. Doing so tends to alienate people around here, which is why I stopped doing it long before I had the baby. The thing is though, motherhood so isolating. If I’m already going to be persona non grata among the locals, why am I also isolating myself from, well, me?
Some days (like now), that’s those linen drawstring pants and baby tees. Other days, it’s one of the sultry sundresses I bought in a burst of postpartum defiance. And sometimes, yes, it’s leggings and black metal tees, because I’m haven’t gotten an uninterrupted night of sleep in 12 months, and I occasionally can’t be bothered to pretend that I have.
Alta has softened its suggestions a little, or maybe I’ve just started to read them differently. I still laugh when it tells me to wear tall boots and a mini dress to the library, but every once in a while, it gets it right: a simple, elegant look pulled from the depths of my wardrobe that reminds me that I’ve “still got it.” Not for anyone else but for me. (And maybe my husband, who would be content to never see another pair of sweatpants, even the Rag & Bone ones, which to him, might as well be from the old lady section of Walmart.)
I’m not chasing reinvention, or even recognition, but a small reminder that the versions of me I’ve cared about still live here, and I can indulge them in my own way every now and then—the one who wore heels to happy hour, the one who wears linen to do dishes, the one who’s learning how to dress for life as it is, not how it looks online. Messy, quiet, occasionally lonely, but still good.
And as much fun as a slinky dress and gin gimlet after work once was, these days, a sundress and a High Life Spaghett on the porch with my husband feels just as special.
I’m not sure Alta was designed for women like me, the ones who’ve lived a few lives already and are still finding ways to stitch them together. AI is a mirror; it reflects whatever you feed it, and my Alta app analyzed my wardrobe to see a woman I used to be. Someone I occasionally still am, in very brief flashes.
I didn’t hold onto these clothes because I thought I’d get to be that woman again, I held onto them because it’s hard to believe that life moves so quickly. One day you’re swapping sneakers for heels in a startup bathroom. The next, you’re folding the baby’s laundry—clothes that haven’t fit baby in weeks, and will never fit again—wondering where the time went. This is the life I dreamt of while I was doing the other thing.
The beauty of it, I’ve come to realize, is that I can choose now. I can wear the slinky dress, or the hoodie and hot pants. I can be the woman who dreamed of this life, and the woman living it. The one who wanted more, and the one who’s learning to enjoy what she has.
I’m not trying to go back. I just want to carry the past with me in a way that feels light. A sundress here, a pair of heels there, little reminders that I’ve lived other lives, and they mattered because they got me to where I am. The rest of the ghosts can stay tucked away for now: not forgotten, just on reserve. After all, life goes by quickly and this era won’t be forever, either. I’ve heard that even Litas are making a comeback, but that’s a discussion for another time.