I asked Grace Valentine to be on Highsnobiety’s September cover over Instagram’s direct message.

“yooo, let’s do it,” the 23-year-old responded. It happened just like that, in all lowercase letters. This sort of virtually intimate interaction is common among my generation. The DM, a means of communication used to flirt or exchange niche memes, is also a functional professional platform. I can’t tell you how many photographers, stylists, designers, and writers I’ve discovered and befriended solely via social media. But my DM to Valentine is one particularly notable instance. No agents or long-winded emails — just two people talking like people who knew each other.

I first scrolled through their feed in 2020: @imnotgrace is a working runway model. They’re non-binary and originally from Pittsburgh. They are friends with Tyler, the Creator, and Montell Fish, among others, and their song “Getaway Car” is all over TikTok. They’re also that model who went viral last September for taking their shoes off mid-runway at Fendi. But what initially caught my eye was their specific sense of style that appears effortlessly curated: Supreme boxers under baggy cargo shorts and men’s dress shirts paired with rare pieces from Stüssy, Dries Van Noten, Yohji Yamamoto, and Carhartt. Valentine is like most young people who pay attention and have the means to engage with luxury fashion and streetwear — except there’s something else, something complex, even intriguing, that comes through in person.

They’re wearing a Bottega Veneta button-up over a Hanes T-shirt with brown Dickies when we meet for dinner at Casino, a dimly lit restaurant on the corner of East Broadway in Manhattan. It’s the type of lively space I’d guess someone like Valentine would want to spend their Friday evening, but I’m surprised to find them tucked away in a corner, hiding from the swarm of Sambas sneakers and Wales Bonner jersey-wearing masses. Later, they’ll admit they came to Chinatown for me.

Montell Fish tried to get me to come down here last week,” they say, “and I was like, ‘Hell no. I don’t want to go to Le Dive.’”

Their swift ascent through the fashion industry might have something to do with it. After only one month of test shoots in 2019, they were catapulted into Vogue and declared a face of Louis Vuitton (“I’d see Virgil around the house; I loved him so much, his designs have my name all over them”). That was just the beginning. Today, Valentine is plastered across billboards in every major European city. They walk for brands ranging from Zegna to Chanel, Ralph Lauren to Missoni. Just last week, I noticed their face above the KITH store on Lafayette Street.

It’s not a shock that the industry is drawn to Valentine. They’re undeniably photogenic, casually sample-size, and a cool six feet tall. They’re athletic (“I used to be a pretty good breakdancer, by the way,”) and sit across from me with nearly perfect posture. I assumed our dinner would be similar to meals I’ve shared with other subjects — some come full of talking points from an elusive agent — but Valentine quickly reveals themself as surprisingly open, introspective, and direct. Within minutes of meeting, Valentine is ready to go on the record about everything, explaining, “I’m an open book. And I’m speaking from the heart.”

We start with the Fendi show last fall in Milan when they were called out for “not being able to walk,” which was actually just them taking off their shoes on the runway. “I kept saying I couldn’t walk in the shoes to everyone who would listen backstage. And everyone just said, ‘Go out there and have fun,’” Valentine says, rolling their eyes. “Go out there and have fun?”

I remember the show all too well. It was on September 21, 2022 in Milan when Valentine stopped mid-runway to take off a pair of bright green wedges. It wasn’t clear if Jones had choreographed a mid-show spectacle or if it was a legitimate mistake until Valentine posted the video of the moment to their Instagram. “thank you “ @fendi we’ll get it next time <3 🧼 #accidentshappen #noshame,” they wrote in the caption.

The internet exploded. Before the end of the show, Valentine’s bare feet were all over my TikTok. Google searches spiked: “Who is the barefoot Fendi model?” Anyone chronically online could have predicted the moment’s virality — the internet’s obsession with model mishaps and runway slip-ups is a tale as old as time. But across from me, as we sip on Diet Cokes, Valentine shows no signs of distress. They calmly say without breaking eye contact: “I wasn’t embarrassed. I was just mad at the team for not listening to me. I even DMed Kim Jones and apologized afterward. He said, ‘Next time, just come to me.’”

Jones and Valentine have been friends ever since. This doesn’t surprise me in the slightest; there’s just something alluring about Valentine.

Almost 24 years ago today, Valentine was born in Pittsburgh. They attended but never graduated from Avonworth High School. Their first job was at New Hope Gracious Personal Care: “I’d just hang out with old people all day. I did it because I honestly felt so bad for the people I met there who didn’t have families. For Christmas one year, I brought all 70 residents gifts.”

Growing up, they also felt alone, just for different reasons. “If I dressed more masculine, I’d get bullied for it, and if I dressed feminine, I got bullied for it,” Valentine says. But this wasn’t strictly to do with their gender expression — as far as they could tell, no one at their high school “had style” nor was interested in fashion. “People wore Under Armour and shit,” they add.

Eventually they found streetwear and, more specifically, Supreme (“They’ve fallen off, though. I mean, they just released a charcoal grill?”), which they shoplifted from a place called Zeds near their house. “One day I’ll drop them 2K [dollars] as an apology for all I stole growing up,” they say, releasing the kind of rueful laugh that comes with remembering adolescent decisions. It was around this time that they started to vocalize they weren’t straight, either. “I just always knew I was gay,” Valentine says, but it was their first serious breakup that fueled “this whole fashion thing.” (One brutal text message from their now-ex, which put an end to their three-year relationship, to be precise.) That’s when their mother took them to New York for Pride and when they were first spotted by an agent. It happened the way it does in the movies: in Times Square, at the age of 19. Fashion was the perfect reason to move to New York. Living in Manhattan sparked more than just professional milestones. “Surrounding myself with people who were constantly discovering new things completely changed who I was and how I dressed,” says Valentine. “I really started questioning myself at this time, too. I actually went back and forth with, like, if I’m a girl or a boy, or if I’m trans. It freaks me out to think about that time,” they say, moving closer to me. “It was a really overwhelming year,” they add quietly.

Initially, they assumed their identity would be welcomed with open arms. Runways are becoming more inclusive of gender non-conforming and trans individuals, but the divide between men’s and women’s fashion runs deep. Everyone who touches fashion is at some point faced with choosing “men’s” or “women’s,” and Valentine was no different.

“The non-binary thing is not a thing in fashion,” they say definitively, looking around at the increasingly packed restaurant. Valentine acknowledges that they certainly aren’t the first nor last runway model to feel this way. “I get misgendered more than anything at castings and shows. I get so pissed off.”

Unfortunately, it’s not just fashion. In 2023 alone, 560 anti-trans bills have passed in 49 US states. “The world hates trans people,” they continue, and though I wish it were different, it’s hard to disagree with their assessment. It’s also hard not to fault Valentine for what seems a painful awareness that all this — the runway shows, the long photoshoots, and prominent billboards — may not be a sustainable career path. They are at the center of a cultural inflection point, and that’s not easy. “Even if I wanted to be in more men’s shows,” they say, “the clothes don’t even fit me.”

It’s admirable that Valentine doesn’t just detest this reality. Instead, they seem energized by their place in it — two beats later, they’ve moved back to the topic of fashion week’s perpetuation of gender essentialism and dysmorphia. “Honestly, I always get depressed about fashion,” they say. “Fashion is really tough on my mental health. It’s all a mess.”

Certainly, modeling could be challenging for anyone’s mental health since it’s an industry reliant on appearances. Even brands that claim to be behind non-binary and trans rights continue to only make clothes for those that present a certain way. But right now, Valentine is referring to something else too, and that’s their borderline personality disorder, which impacts one’s ability to self-regulate and significantly increases impulsive, self-destructive behaviors. I read about this on Valentine’s Instagram earlier this year. On May 21, Valentine posted in support of Emotions Matter, a non-profit organization formed to educate and advocate for people impacted by borderline personality disorder. Now, sitting across from me, they want to make sure we include their BPD diagnosis in this story. “I’ve got so much help for it. I just got out of rehab. I was there for 30 days. I’m feeling so much better. I’m going to be okay.”

“My Highsnobiety cover is the first project I’ve been excited about since I started modeling because I loved what I wore,” they continue. As they speak, I begin to consider the complexity of our situation: Valentine is calling out the challenges of fashion — even as they hold a position that so many would kill to be in — in front of me, the editor of this magazine. Although we seem to connect over shared fashion heartaches, this might impose a kind of natural division between us — we’re clearly facing the same questions from different angles.