Hate to say it, but AI did a great job making outfits for me

Hate to say it, but AI did a great job making outfits for me

Leandra Medine Cohen

Sep 29, 2026

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This newsletter send is brought to you by Yahoo Scout.

There are so many things to dress for in September: back to school, back to work, back to a quality of life that doesn’t support a pair of lightweight, flamingo-pink silk trousers and a deliberately wrinkled cotton button down shirt. It’s like even if you’re just crossing the street to pick something up from the store, this month demands a quality of polish that hasn’t existed in the visual lexicon for like 3 months.

Live footage of an outfit I wore to get milk last week:

Nili Lotan

knit (I got a small; colors on

this one

are great too) styled over a

Venroy baby tee

with

Aflalo

‘Tavi’ pants (the capris are

here

, but the most important news of the day is that

they’re coming in pink wool

) and

Gabriela Hearst’s

cowboy clogs

It can feel a little confronting or jarring at first and then turn into full blown frustration — the kind of false-alarm identity crisis that has you questioning whether you even have personal style anymore, where it went, what it was. But I have become so intimately familiar with the grooves of this month — how confused I could get standing in my closet among clothes I love that somehow feel wrong, how bad the subsequent outfits can be, how much worse that makes me feel — that I know better now than to pour myself into the task order to nailing a look these days. Feel good enough, I tell myself, just get by. It will all make sense again soon.

But this year in particular, there have been EVENTS. The kind that spill into each other on the same days-into-night: back to school eve at my kids school, followed by a store party I would be hosting; celebratory work dinners, social dinners, Jewish holidays. Fashion week, and so on. So I tried something different — I asked Yahoo Scout, Yahoo’s AI-powered answer engine to help me get dressed for four such occasions where I could not for the life of me generate my own look. I know the popular opinion is to feel frustration/fear that AI is going to replace us, but I strongly believe that if we use it correctly, it’s more likely going to enhance us.

Rohe

fitted ivory blazer with Emi Mess pants (

these

are comparable and will actually make this a suit),

Gabriela Hearst

cowboy mules (have and wear

these

a shit load too).

Cordera

belt and

LMC

turquoise choker (tysm to the 4 people who have already purchased her!!!)

Here’s

the choker once more, and two of

the cuffs

. You can write to me directly about rings! ‘Chai’ pendant (clipped into belt) is

here

. One more time for

the jacket

. Yahoo Scout really wanted me in fancier shoes but I didn’t have

these

yet, so clogs it was.

The most surprising discovery of this practice is that the ideas Yahoo Scout had did a pretty good job initiating my own sense of style and creativity. For example, when I told it I needed help figuring out what to wear to a celebratory dinner for a well-known fine jewelry designer, it suggested an “elegant trouser suit,” which then had me thinking about ways I could twist the mandate. So I put on Yahoo Scout’s rec (above) then went ham on my own —

Liberowe

silver jacket — my game over piece of the season, no question. With

brown Aritzia pants

(cannot recommend enough; have them in a size small in this color, and

a medium in black

[I roll them over like 4 times] they are versatile as F),

Christen

sandals. You know my feelings on

these

too — can’t go wrong

If you want a higher waist pant, I have and love

these from Spanx

too. Mine are

black

but I think

navy

is the right color for this year. With

white

c-boy boots [o guys! Someone put my

Pradas r on Vestiaire

] and a

silver jacket

? Yaaaa If you prefer gold for your opulent outerwear,

she

is pretty gorgeous too (and the boots then should be like,

red

).

This cutie jkt from Oscar

is definitely right for one of us.

Here’s

the zip clutch!

Not exactly a suit (and not rendered in the material suggestions AI had: (“luxury fabrics like crepe or satin”), but a shirt and pants nonetheless. Second look definitely more fun, but I think the first was actually more appropriate, so I went with that.

The second prompt:

One thing I realized while I was getting help getting dressed is that the more detailed I was, the better. A lot of the initial answers were too conceptual, and I needed concrete descriptions, so I would further define by asking the engine to describe the outfit to me (and I must say that not having a visual actually helped me apply the ideas to my own wardrobe better.

Smythe

sweater (I think it’s our

year of sleeveless chunky knits

),

The Row

pants, black sandals that could/should be replaced with something like

these

(or kind of love

these

?) for cooler weather;

Hunting Season

bag

Cream trousers, neutral knit. But then I realized, you already asked me to wear cream trousers so can I take some creative license please and instead try a pair of velvet trousers?

Same sweater

, this time styled with

Soeur

velvet trousers (for sure

these

if you prefer corduroy), which I got 1 size bigger than my normal for an even baggier fit. The sandals are

Versace

(with the

right knit socks

,

these

are fab too, but if you’re looking for a closed toe, I wouldn’t dissuade you from

these

either).

This bad boy

for clutch!

Bicep bangle

here

, earrings

here

.

She’s

going on sabbatical soon.

Which I dutifully did.

In my own estimation, I decided to get a little cheekier in lieu of the neutral knit but stayed with the cream (adjacent) trousers —

Orzo

silk scarf (vibe is v much like

this

, or

this

, or

this

or my fav —

this

),

Giuliva Heritage

deep scoop neck tank,

All Three

‘Zina’ pants,

The Row

kitties and the same

Hunting Season

bag

Hairbrush

, toothbrush, Curad gauze pads for my daughter’s elbow rash. It’s much better ty for asking!

Next: what to wear to work.

Nour Hammour

trench coat,

Aflalo

button down (the color is gone, but

she from Comme Si

is close),

B-low the Belt

belt,

Doen

jeans,

Staud

kitten heels (dropping in

these cuties

on more time too. They are very good!!),

Vincent Boulevard

sunglasses. Container necklace

here

My own look — which was actually inspired by some of the mandate in the AI-look (light jacket, t-shirt).

The Row

jacket

and

shoes

(my plan is to futurewise wear her with

red leather gloves

and

navy flares

), a graphic tank,

Tory Burch

skirt (

this

is the one I wore in the J. Crew campaign),

L.L. Bean

tote. The pearls are Marisa Klass! Maybe you can do something like

these

or

these

.

I’ll never dissuade you from a

Venroy bb tee

!

And finally:

Vintage jacket from my grandma, which you can get as this,

here

. I have my eye on

this thing

too.

Venroy

tee,

Antik Batik

pants (again, for alt corduroys, it’s only

these

, or honestly, actually, I also like

these

),

Gabriela Hearst

clogs

Yahoo Scout suggested

corduroy pants

, which I thought was an inspired idea, and a clean line belt or layered necklaces. I replaced the layered necklaces with bracelets, which felt like it took care of what the belt would do. Was a good soldier when it came to a mid-thigh hitting jacket tho!

See more of my jewelry

here

!!!

In my own estimation, I thought: I’m not letting hairkerchiefs go yet, and a neutral-but-still-colorful one with light sunglasses can bring some levity to an all-black look. Here’s where I landed:

Soeur

silk head scarf (but tbh,

cotton

is better; as an aside,

this thing

is tiny but soooo cute?), Aflalo ‘

Brein

’ shirt (waiting patiently for

this bad boy

too) and ‘

Bradum

’ trousers (world’s greatest, still).

Tory Burch

basket bag and

Vincent Boulevard

sunglasses (so hot on

these

too for the look here). Pinky ring

here

, and I have exactly one of these pendants in stock. Call me!

Aritzia

pants could be a good alt here, especially for a weekend hang. Sneakers are Polo Ralph Lauren (kind of obsessed w

these

and

these

as an alt? So good in the

purple

! With a

freaky red knit

, obv.). Bensimon’s are a good alt if you’re after something even more similar.

I liked my look more in this instance, but am not sure I’d have gotten here without the engine’s initial call (it recommended

non-sport sneakers

but I took creative license and went with with my

c-boy clogs

).

In sum: I am feeling pretty confident that AI won’t replace us but that it can help us. Call me an idealist! But when you can’t think of what to wear, you’re bound to, at a minimum, get good ideas that can be slotted into the framework of your own closet, built from your own creativity, to reflect your tried and true, very human personal style.

The end!!!!

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