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The Cereal Aisle by Leandra Medine Cohen · 2026-09-08 · 6 MIN READ

What the hell to wear this week

7 days 7 outfits

Leandra Medine Cohen
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Early September has got to be the most precarious time to get dressed. It’s still hot, but it’s not summer summer, so the public pajamas and ode to sweaty nights just hit different. In September, they feel like an awkward morning after.

And if you’re in an era of life where it matters to you that you look put together when life resumes full speed, but also find that it matters to you that in getting dressed, you create visual harmony with your environment, your closet can really like a pickle you’re stuck in.

How do you accommodate the similar temperature and the fact that you’re really to feel different without rushing out to buy things you can’t even wear yet? (On this note, I did get this poncho.)

Allison Bornstein has wrong shoe theory, maybe the transition season dressing formula is similar. Not quite wrong shoe, but wrong shirt or hat or dress or pants. Basically assembling yourself into a clothing equation that represents 1 part future season + 1 part past season + neutral, seasonless item and then any curveball or cheese wedge you want to throw in as the way you make the look uniquely you. Let me demonstrate:

In the spirit of the math: the past season item are these sheer slinky baby pink pants I’ve been wearing all summer (pink denim suggestion this way; an alt in a more fall color is here from Ayr; don’t miss this sheer button down while you’re there), the future season item is the houndstooth fringe jacket, the neutral is the graphic t-shirt (in a good color for the upcoming season!) and the flair — less curveball more outfit finisher are the loafers and clutch.
Liberowe jacket, Guizio t-shirt, The Park pants (these are the fall friendly pair. I love in the navy), Liffner bag (green lizard is avail here; the pushlock in the same burgundy croc finish is avail here) and Emme Parsons loafers

If it’s really hot and a jacket is out of the question, one tried and true method that will almost always hit is to go long on summer, but in all black —

The layers here are cotton poplin (Donni shirt — if it’s colder, a slightly but not too cropped, kinda boxy but kinda shrunken cardi like this will do the trick, and Amotea shorts: this v-shape is flattering; here’s a good fall alt and because I’m me gotta show you these too) and the sleek sneaker/tote combo (The Row — or this newer but on sale pair?, LL Bean) brings an air of have shit to do, while the slicked back hair/sunglasses (Jacques Marie Mage) and fancy jewelry demonstrates that you care what you look like while doing it.
Bracelets and rings are LMC Fine, the necklace is Year of the Flood.

One of my favorite constellations brings in a pair of pants I wore pretty much everywhere this summer from the beach and the pool to dinner and a walk and in one stupid instance, even to a Pilates class. These are specific and whimsical and very bright so while the future season item (the long jacket) serves its purpose, it’s really the closed toe suede shoe that can go either way which really works to make this make sense —

The Serious Bag helps too. Rose Room jacket, cropped graphic tee from Depop (love this men’s one from JW Anderson), Pointe Milou silk pants, The Row shoes, Ray-ban sunglasses (you know what I’m gonna suggest…) and my own ‘single tile’ double wrap necklace. Tiger eye is a great way to make it feel like fall is knocking.
Here she is in the shade. Makes a diff no? The other tee silhouette I love is this one from All Three (esp in navy) and this from Eterne. You know I’m gonna push the Venroy destination shirts on you one more time too.

In the reverse direction — when you wanna go summer top but feel more serious below hip:

Thistles sunglasses, Beaufille tank, All Three pants, Cordera belt and Manolo Blahnik’s ‘Susa’ — never more relevant than during these first weeks back. The turquoise choker is LMC. Dm to order!!

Wore this to my older girls’ first day back to school and then a work breakfast all the way downtown on Vesey Street.

Layering, on balance, is proud the best of your bets. But not the kind of layering you think! I’m hot on sheer shirts over opaque/graphic tanks right now:

Nili Lotan lace up georgette top (it’s here in black; great alt here), Staud tank, High Sport paisley pants (still into the belt loops too), Gabriela Hearst cowboy clogs
Same single tile necklace, Liffner clutch. Crushed velvet is pretty good too.

Or something similarly flimsy, but also very summer-y, with something more covered up under it:

Versace (pre-Dario!) fitted button down (you’ll find the closest approximation, fit-wise with vintage Cavalli; my eye is on her), Frankie Shop shorts, and the Gabby clogs again. Truly the bizarro Dutch clog meets-the-old-west I never could have imagined I would like this much.
Vincent Boulevard sunglasses, which I similarly cannot recommend more for a subtle but modern 70s feel, and Nili Lotan’s basket bag

Also for layers, but this time with a tried and true summer slip —

Not the Ingrid, if you can believe! Magda Butrym’s white silk lace-hem slip dress styled with an Elder Statesmen knit over (found her on TRR, here’s one more), LMC’s classic container necklace and tear drop earrings, plus the same Vincent Boulevard sunglasses in black.
And suddenly, I am obsessed with kitten heels. Can’t stop thinking about them, styling them, looking at them. These ones are so good because it’s such a lady shape but the distressed leather gives them an air of cool. Love these from Prada too though, and you can’t go wrong with Jimmy Choo’s these. Also got these from Staud, and they’re good.

Last look is my favorite look and finally makes use of this incredible Roger Vivier vest I received as a holiday gift last December:

Isn’t she something? Wanted to bring in some turquoise to pay tribute to the fringe but a necklace seemed too obvious, so the bag (Liffner; different vibe but here’s damn good clutch for $310 from Staud). Vest is Vivier and here are great pant alts (casual from Kondi, buttoned up from Giuliva, somewhere in between from The Park) to unleash your extroverted flair for the season ahead. This is the bag to compliment, no?
Obviously you can find a delicious second hand alternative — a couple here and here for you but I have to say if you’re going this way, the glitzy belt (Roger Vivier; here is an alt from Dehanche) really does good work knocking the vest off its skis.

The month is actually unfolding, so more ideas are coming to me. Expect a sequel next week — same place, same time. Until then, I love you!!!!

Leandra

✧

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