158: Leandra Medine Cohen seasons the dish

The godmother of fashion Substacks on summer tumult, ego dissolution, and boat shoes.

New York has never before had a Leandra Medine Cohen, and it’ll never have another. How does one introduce someone who is, almost as a prerequisite, already familiar to anyone subscribed here? When she first became known to us, her work with Man Repeller offered up a framework to a generation of fashion types that placed equal weight on the power of relatable writing and meritocratic personal style. It served as the foundation for this present wave of newsletters, which she now, too, has been surfing with The Cereal Aisle by Leandra Medine Cohen since the very beginning. It’s exactly what you would expect from a true original who can feel the seismic shifts of industries before they register on the Richter.

I spoke to Leandra—a few times, actually—for this newsletter, getting the chance to observe her mind at work in outfit practice and outfit theory and back to outfit practice like some gorgeous fashion mille feuille. What I can say over these months of getting to know her, is that Leandra understands the medium of fashion deeply in the roles it plays on expression and identity. And that her insuppressible maker impulse also spouts out a signature style that’s emulated abound—but no worries!—there will always be more, new, original ideas where that came from.

Here, in her own words, Leandra shares what she’s been buying, wanting, wearing, and wondering.

LR: Last time we chatted, we were in a weird funk with summer not being what it should’ve been, and then fall had, like, two weeks of normalcy. Now we’re here. LMC: Part of what was happening with my funk this summer is I was pregnant. I knew from very early on and miscarried in September at 10 weeks. Throughout the pregnancy, I was running through this psychological negotiation where I felt like, “I know what it is to be pregnant and have a child and how much slow-down it requires, and I know that I’m going to want that time.” I look back now towards the end of Man Repeller and the time between then and my starting on Substack and I would not give up that time with my kids for anything. If that meant killing off an identity to really become a mom, it was worth it.

When I got pregnant this time, I felt like there was all this new momentum behind me, I was in a groove with my work. I felt like I had a good understanding of what my newsletter gives to its subscribers, and I was excited about the work. It’s been a bright spot and sometimes an anchor in my days and weeks, and I just kept thinking, I don’t want to give this up. The pregnancy really felt like my reconciling whether I would actually have to, and that question was like a pressure cooker on my summer. I was sort of trapped in this zero sum mentality that didn’t, I don’t think, reflect the truth of what having a next baby will mean.

During fashion week, I started to feel excited and inspired again, and my body was changing and I was settling into it in a really tender way. It burst me open. I got excited to get dressed and was thinking so much harder about how to convey style through the upcoming changes. I think because of the constraint, I felt more creative. Change is daunting at first, and then you crack it open, and you’re like “I got it!”

I was expecting to want to wear a lot of flowy pants, similar to The Row Gala pants. I got a great pair of brown ones from Vince. My ass is always the first thing to grow when I’m pregnant, so I was planning to wear a lot of dusters. I was definitely thinking about the challenge of making my body reflect what I wanted to communicate and how I wanted to feel. In my previous pregnancy, getting dressed became so much about proportion—as my belly got bigger, I wanted my pants to get tighter, and I specifically wanted A-line shaped swing coats to balance the proportion. It’s like completing equations. Outfit ratio equations. You were balancing the dish.

The first time I was pregnant, we were still deep in the era of athleisure, so it was easier to get away with wearing leggings and still feel like you’re conveying a point of view. This was also the peak of voluminous clothes: The Row was really rising. Rosie Assoulin, a designer whom I was really plugged into, always drew me in with big pants and roomy tops, so it felt like the shape of fashion reflected dressing for broader body types, anyway. You can say that’s true now, also, but I have been so zeroed in on the hotpants, you know? The tight dresses. Everything that’s tiny. So it was a less straightforward mental transition this time around.

In the time since—it’s been a month, I guess?—do you feel like any of those style thoughts are still with you, or have you landed somewhere different than where you were before? I have not…they felt more like a function of practical circumstance than anything else. You know how every few seasons, you will start to feel the pull toward discovering a new style identity? I was getting that inkling, and now I’m feeling more like the identity is coming together—all the ways that we are going to want to dress next year and the year after and the year after, I’m starting to see it, it’s starting to make sense in my head. This is going to sound dramatic, but it does require a bit of ego dissolution and identity collapse to recognize that you’re not a former “you” anymore, those favorite jeans don’t make sense and probably won’t make sense again for a while. 

All I can think about wearing, the only thing that I’m excited about wearing, is a pair of wool flannel—a really fine fabric—think Brunello Cucinelli gray pinstripe pants that just fit so perfectly and flare exactly the right way. They didn’t need to be tailored and hit so they’re not actually touching the floor but look like they are. I’ll wear them with suede moccasin booties, which are one recent purchase that I do not regret, that I’m sure makes no sense to most people—The Row’s Tyler moccasins that look like Minnetonkas without the fringe. I love them and I wanna wear them and flare pants with a rigid cotton t-shirt, like the ones Bode makes. This feels like a Leandra outfit. It’s the contrast. It’s all the different elements. If I’m not wearing a rigid t-shirt, then I’m wearing a fine-knit sweater with a jacket over it, and a crown. A crown! I was just talking to Jalil [Johnson]—He turned me on. It’s really crown season. He’s gonna make it crown season. What is the crown that you’re gonna wear? I want the Bode one. That stupid $530 elastic beaded thing. It’s so beautiful. Can you imagine that with a pinstripe suit? On you, yes. It would be amazing. So I’m there, I’ve been able to get there, and that feels good. 

This is going to sound dramatic, but it does require a bit of ego dissolution and identity collapse to recognize that you’re not a former “you” anymore, those favorite jeans don’t make sense and probably won’t make sense again for a while. 

What else have you purchased since we last spoke, which was two or three months ago? A color I’ve been thinking about a lot is this slime green, not exactly chartreuse, that Prada green. I want an element of that green in every single one of my outfits. I’m cultivating this theory about color and how to wear it in the context of a pretty basic wardrobe, ‘cause I’m also kind of gravitating toward this electric violet purple, and I over-indexed on red, but it’s still there, and then buttery yellow, which has also been in and out. The neutral colors that I think of as they relate to a fall and winter wardrobe are brown, navy, black, khaki, and gray. It feels like the obvious way to style the green would be with the brown, very earthy, but I really like it with shades of ivory and khaki and white, it feels a little more unexpected and allows the green to be a “pop.” So, I’m anticipating those pants with khaki button-downs and long strings of pearls. You’re remixing the neutral, rather than the accent. Same thing with red, you don’t expect it to work as often with shades of heather and charcoal gray, but it looks so much better when you do it. It doesn’t get swallowed, it floats on top. Yeah. And it’s not as polished as when it’s with black, it’s not as preppy as when it’s with navy.

Let’s circle back to fashion month. Are there any specific pieces that you’re like “I’m for sure getting this”? I felt like that about the Bally boat shoes, no question. I was really inspired by Milan. The emphasis seems to be less on the actual clothes than on the way that the clothes are carried, that feels like the whole raison d’etre of Milanese style. I think that’s what felt so relatable to me about Bally. 

I was really into Bally when that collection showed in Milan, and I wrote about it a little bit, and then the creative director Simone [Bellotti] wrote to me and said “I’m such a fan, you’re on my moodboard.” It was the utmost compliment. He asked if I wanted to sample anything from the collection, and he sent me the black leather suit and the shoes—they’re better in person! The jacket is single breast, and it swings out ever so slightly, so you get this volume, and it creates an amazing shape with the tiny tap shorts. I’m like “this is exactly how I want to dress right now. A little preppy, a little glamorous, a little messy.” Miu Miu nailed that too. I was getting such Midwest thrift store vibes from Bally, like an idealized version of that. It’s amazing how different our references can be based on our prior experiences.

I think we all have nostalgia for our comings of age. It’s the same way that, when I watch The Devil Wears Prada, it always touches me in such a warm place. It was a formative movie moment that aired just as I was coming up. You’re like “I am Andy.” Those cobblestone streets, in a slingback? It me. It coincided with my stylistic individuation. I graduated high school in 2007, so I was coming out of my Yeshiva Day School skirts and elbow-length shirts, and I felt free. The world was my oyster, I could wear whatever the hell I wanted. It was like “Okay, my closet isn’t a function of mere necessity any longer, I get to make choices,” and so when that movie came out was among the first times I had eyes, in a lot of ways.

I have this very specific memory of, maybe it was SS08, where I just gobbled up the runway. I loved Phillip Lim—that was when Christian Louboutin was still doing his shoes—and that was peak Alexander Wang. That's when contemporary American fashion was becoming luxury, and it was just such a fun time in New York fashion. Proenza’s moment. Nicholas Ghesquiere also contributed in a very significant way to the drool that was 2008-era fashion. Remember the structured floral mini dresses from Balenciaga with the gladiator sandal boots? Heaven! I find that I'm constantly trying to recreate that feeling.

What are your outfit credits right now? What are you wearing? A Ven Store cardigan…RIP. Did you shop the closing sale? I did get two more pairs of track pants from Charlotte, once she was done…I lived in those track pants last year. That was another thing that I thought a lot about last summer, I was like “I think I’m gonna wanna wear a lot of boat shoes with cashmere track pants next winter.” The prescience! I bought these weird Sebago boat shoes with fringe when I was in Milan last May, like “I don’t know why I like these, but I’m being called to own them,” and then they came so in handy when I was recreating a Miu Miu runway look last month.

To continue: a Loulou Studio sweater—I had this on from this morning with a pair of leggings after drop-off. A Saks Potts belt. It’s a good one. Loulou Studio jeans, also. I’m wearing so much Loulou Studio because it arrived yesterday, I just didn’t have to think. The Bally shoes. And the coat is Tory Burch. The earrings are Ana Khouri, I’m test driving them. She does special collections for The Row occasionally, and these are from the most recent capsule. They’re based on the ear cuff that she make, but they’re actual earrings. Don’t they look like diamond AirPods? They’re like the cooler equivalent of a pair of diamond studs. Maybe the vibe is…daughter of a matron. It feels a bit like “Mom, I hate you, but I’m also of you.” That feels like it taps into your fashion roots…the Upper East Side, and the rejection and re-embracing, the remixing…It is just one hand gesture away from an illicit cigarette…styled maybe with a car coat, some disheveled hair. I think that’s a vibe. But I’ve certainly come full circle with where I’m from.

There’s something that’s really intoxicating and exciting about figuring out how to dress yourself as your body’s changing. The goal is not to keep your body the same all the time, it’s to navigate and get comfortable with how you will have to think differently about interacting with it as it evolves.

Earlier, we were talking about fall dressing—for me it’s like this fun puzzle that you start putting together, like “This is what I’m gonna look like this season.” I can feel little elements of that now, I’m gravitating towards the smallest dose of whimsy in every look, which is maybe a form of trying to find some levity, of trying to find the strange accent that makes all the tried-and-trues feel less “done,” basic, finished, has-been. The “who am I gonna be for fall” thing. Is it who you thought you were gonna be, or are you kind of recalibrating that? Definitely not who I thought was gonna be, because I thought I was gonna be very pregnant.

Interestingly enough, all of the style content that I produced over the end of August and September was done while pregnant and trying to figure out the equation of how I’d dress and how that would be reflected in a helpful or still service-y way for the newsletter. And that work felt like it was some of my strongest. That doesn't get lost on me. There’s something that’s really intoxicating and exciting about figuring out how to dress yourself as your body’s changing. It’s like, the goal is not to keep your body the same all the time, it’s to navigate and get comfortable with how you will have to think differently about interacting with it as it evolves.

This interview has been edited and condensed for clarity.

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