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It’s one of the most annoying dilemmas women face — wanting to look stylish at work, on weekends and on nights out, but getting stuck in a rut.
At the same time, finding the budget for standout pieces — or the hours to hunt online for clothes that actually flatter your shape — can feel impossible.
Personally, beyond the trial-and-error misery of online shopping, I’m burned out from slogging through fast-fashion stores and “basics” sections — a far cry from the joy I find in thrifting.
Between wildly inconsistent sizing, sometimes even within the same store, and harshly lit fitting rooms that seem designed to humble you, it feels like a losing game.
Add to that trend cycles that change faster than the seasons, making it impossible to know what I should be buying, let alone what actually looks good on me, and going shopping can feel less like self-expression and more like a personal test you’re destined to fail.
If money were no object, the obvious fix would be a personal stylist — but for most women, that kind of help remains a splurge, not a solution.
But two new AI-powered start-ups want to change all that — claiming to help you find what looks good for your body shape, doing the hard work of sifting through the online retailers for you, and democratizing previously out-of-reach styling for every woman.
After years of second-guessing what actually works on my body, I decided to try them out and compare how they fared in real life.
Could they get me out of my fashion slump — without sacrificing my individual style?
ShapeShopp’s body-smart AI helped me see my curves in a whole new light
My first styling consultation was a Zoom call with Amy Wister, a former personal stylist and co-founder and CEO of ShapeShopp.
The platform — which offers eager customers a three-tiered membership plan, ranging in price from $9 to $99 a month, depending on how much style help they need — is built around a soon-to-be-patented system that identifies a person’s body shape based on the relationship between their shoulders, waist and hips, not their usual clothing size.
After that, the technology — which has been trained to recognize clothing attributes like necklines, pleats, waist placement and pant shape and scores them according to how well they work on different body types — assesses clothes across a huge database of retailers and assigns the right ones for you.
Then the humans come in. A team of ShapeShopp stylists curates weekly shoppable catalogs from those selections that align with your style goals.
The endgame, Wister said, is to dramatically reduce the frustration of online shopping, where most women fail in the fitting room “six out of seven times” simply because they’re choosing the wrong shapes, not the wrong sizes.
But first things first — my body shape. For the assessment, I wear a skintight black bodysuit and leggings, and within minutes I’m told that my body type is “green” — meaning I have narrower shoulders, fuller hips, and a defined waist at the top.
ShapeShopp’s solution? Making sure I buy clothes that create more balance.
Rather than hiding my hips, Wister stressed, it means giving the upper body — especially the shoulders — more visual weight so everything feels proportional.
ShapeShopp’s search of “green” body-type appropriate dresses includes an Aritzia dress for work that Wister singles out for me: a twill, button-up midi shirt dress with patch pockets, a tie waist, and lightweight fabric with a soft, flowing drape.
It’s not my usual style, but to my surprise, when I try it on in the store, I love it. It immediately elevated my office look, was flattering and still honored the gothic and Parisian touches of my personal style.
In other words, this dress didn’t feel “too corporate” or like something I wouldn’t be caught dead in when out in Bushwick.
For daytime looks, she recommended horizontal or rounded necklines — scoop, crew, square, boat or sweetheart — rather than V-necks, which would exaggerate my shoulder-to-hip contrast.
But for nights out, it’s OK to play with emphasis. Wister’s team recommended a dress I actually already own: the Urban Outfitters Samara Mesh Strapless Midi Dress in the color “red berry.”
Seeing her endorse it made me feel confident in my style choices.
“That’s your roadmap. You have a beautiful figure,” Wister told me, making me finally appreciate the parts of my body I’d long pretended to like — and secretly resented.
A digital stylist that tried … and failed. The AI app mixed my closet into cringe-worthy chaos
After my crash course with Wister and ShapeShopp, I did a test-drive with Style DNA, an AI personal stylist app that turns photos of your own closet into outfit ideas — while also pitching new clothes and accessories from real retailers based on your body type, style “vibe” and color profile.
The $29.99-a-month app unlocks personalized clothing recommendations tied to your assigned “color type” — determined by a selfie that analyzes your skin tone and undertones (I was labeled a “True Winter”).
The app tried to pin down my personal clothing style through a series of vague, oddly binary questions — like whether I prefer short sleeves or long, or whether my body type is standard or curvy — that left me more confused than clarified.
I uploaded photos of my favorite wardrobe staples alongside the pieces that have been collecting dust in my closet.
The app’s styling results? Bizarre outfit mashups — like a floral “office-appropriate” blouse layered over a skintight black minidress as a work look that I would never be caught dead in.
Style DNA bills itself as a digital stylist that can decode your closet and spit out foolproof outfits, but in practice, it felt more like an algorithm playing dress-up with my clothes.
That isn’t to say Style DNA is useless — it might be best for beginners who crave style inspiration or need a low-stakes way to remix their already existing wardrobe.
But for shoppers who want clarity, confidence and a real understanding of how clothes work on their actual body, the app came up short.
Humans still rule: From questionnaires to virtual closets, Natalie Tincher and her team showed me how to dress for my life — not a computer screen.
My last attempt at reinvigorating my wardrobe was to seek advice from Natalie Tincher, founder of BU Style, a Gotham-based personal styling service that puts humans — not algorithms — at the center of getting dressed.
BU Style offers flexible ways to work on your wardrobe — be it offering new ideas and pieces, or ways to work your existing wardrobe better — with memberships ranging in price from $141 all the way up to $875.
During our virtual meetup, Tincher explained how she doesn’t just look at clothes; she “closely reads body language” and considers confidence, behavior and intention.
I completed her Style Strides questionnaire, which asked questions that forced me to think critically about body image, my over-worn pieces, and how to best balance my alternative, vintage-inspired style with professional polish.
Her analysis? I’m dominantly “Creative,” with “Polished” as a secondary influence.
After I uploaded photos of my wardrobe to the BU Virtual Closet, Tincher used our call to style three outfits entirely from pieces I already owned: a polished work look featuring a roomy black sweater paired with a vintage floral skirt, sheer black tights and knee-high boots; a night-out outfit built around my go-to black minidress, layered with a black leather blazer and the same boots; and a daytime social look centered on a pair of jeans I’d been avoiding, styled with a floral corset top layered over a black, sheer lace shirt.
She also recommended some pieces I could buy to supplement, but her focus was more on how I could rethink clothes I already own to keep costs down.
I loved all the looks she created for me.
The investment I’d make myself
If I could, I’d sign up to BU Style in a heartbeat — working with Tincher was a joy, and I loved every minute of it.
Her expertise feels like a daily style upgrade, though for most of us, it’s understandably a premium experience.
Style DNA was a bust — the fully AI-driven styling experience offered frankly bad advice.
But I was also surprised by how great ShapeShopp proved for online shopping: it’s a clever new system that blends tech with style, and is a great, affordable option for women who need a fashion boost.
