I grew up in a tiny suburban town in Massachusetts. I was perpetually bored. On weekends out, I would smoke cigarettes in the Stop & Shop parking lot or, who knows, drive around without headlights on some back road at 1 AM listening to Kings of Leon or something, trying to imagine my life out of there. I always felt like some kind of weird outsider. From day one, I was like, I will get to New York. I am going to make it, and figure it out.

I was literally the only Jewish person in town, and I was fully Jewish. It’s funny, my best friend was an Egyptian Muslim and we were the only two people who didn’t eat pork. There was a small synagogue in the town over, but nothing in my town. I don’t think people even understood what a Jew was.

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I failed the first two years of high school, horrifically. I was suspended for physically fighting and skipping class. I was a horrible child. But I got my act together at the end of junior year.

I realized I was never going to get out if I kept failing, so I did a total 180. There’s this program called the Rotary Youth Exchange that came to my Spanish class and said, “If you get good grades, you can go to any country in the whole entire world, study there for a year, and it’s free.” You just had to pay for your plane ticket. I thought, Well, I’m getting the fuck out of here.

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I ended up living in Crimea for a year.

There were all these great countries to choose from—Austria, Switzerland, France, Italy—and I was like, “You know what? I want to go to Ukraine.” It’s where my grandmother was exiled from, and where her entire family was killed. I wanted to go back because I was really interested in my roots.

That was another thing about being Jewish. I needed to figure out who I was and where I stood in this community. I ended up living in Crimea for a year. I didn’t know any Russian when I went there, and it was a Russian-speaking town.

My host sister knew some English, but I really had no one to talk to. It wasn’t until four months in that I met a Peace Corps volunteer, and befriended her and one of her friends. It was really, really hard but I learned Russian, and that was something that helped me with my career, and, who knows, maybe with school.

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I’m still very close with my host family and, before it was annexed, would visit when I could. I call my host mom “Mama” to this day. My host sister has since relocated to Tennessee. She’s coming to my wedding. I invited my host parents, but they obviously can’t come.

I’m concerned for my friends there, and my friends’ husbands who are there. There was a moment when my sister couldn’t find her husband—it was three weeks of no contact and we had no idea where he was. She has two small kids and she’s essentially a single mother right now. It’s really scary. At the beginning of it all, I was FaceTiming with one of my best friends and all of a sudden a bomb exploded in the background. It’s definitely very, very frightening.

At the beginning of it all I was FaceTiming with one of my best friends and all of a sudden a bomb exploded in the background.

I went to Hofstra on Long Island, which is like Jew Central. I didn’t even tour before I went. They gave me a decent package and it was one of the few schools that I got into, so I was like, Well, they’re giving me decent financial aid, it’s close to the city, I’ll make it work.

It was a totally different culture of Judaism than what I had been exposed to growing up. I went to a religious camp for eight years in New Haven, where my grandmother lived. But I hadn’t been exposed to Long Island and New Jersey Jews. I was like, “Why is everyone wearing David Yurman and they’re 17?” Mental.

Vogue was the ultimate dream, of course.

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I always wanted to get into fashion. Vogue was the ultimate dream, of course. I did an internship at Women’s Wear Daily, in the accessories closet. I did an internship at Marie Claire. I was not a good intern. I also studied abroad for a year in St. Petersburg.

When I graduated, I didn’t have a job and I couldn’t find one in the industry. Web wasn’t a thing. I was taking bullshit gigs at the time. I found a sales job off Craigslist doing cold calls for a Hasidic man, selling memberships to these roundtables with CEOs. I eventually got fired, and then I hostessed and I did some Russian-English tutoring. I was living in this tiny room in Queens next to JFK with two Russian women and doing all this freelancing, probably writing some BS like, “The 10 Best Nail Colors.”

At the time, I was going to Crown Heights a lot because all of my friends there were getting married. In the Orthodox community, you get married at a young age. So I was going to wedding after wedding after wedding. After a while, I was like, Wow, these women are really chic and have just a great look about them. I ended up photographing and doing a whole entire story about their style for Fashionista.

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After that, I decided to go cover the fashion week happening in Kiev. I had kept in touch with my old accessories editor at Women’s Wear Daily, Roxanne Robinson, and I was like, “Listen, I’m going to Kiev. I have a camera. I’m going to go photograph the fashion week and I want to write about it. Can I do it for WWD?” I paid my entire way. I paid for my plane ticket, and ended up staying with a friend.

At that moment in my life, this was the crème de la fricking crème of everything for me. I ended up shooting it, writing about it, and putting on my serious journalist face. I was, what, 23? I didn’t know shit from shampoo, but whatever, I really, really tried. And I got my first clip in print ever. It’s actually why I ended up getting fired from the sales job—because I was so clocked out.

I didn’t know shit from shampoo, but whatever, I really, really tried. And I got my first clip in print ever.

I also managed to finagle a Vogue Ukraine story. I did a Fashionista interview with the founding editor-in-chief of Vogue Ukraine when the magazine launched. Then I got a story into one of their early issues, which was incredible for me. After that, American Vogue contacted me via LinkedIn, if you can imagine.

Someone messaged me, “We have a position open for a fashion writer and we want you to come in.” I was like, “Is this a joke?” I was so broke because I was using all my money to color print my resume on nice paper at Staples. I think I had $60 in my account. And this wasn’t like I had $60 and a Rothschild parent. I literally only had $60, and that was it. I remember screaming on the phone to my dad, “If I don’t get this job, I’m going to have to move back home because this is it for me.” But I got the job.

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When I was at Vogue, I was going back and forth to Kiev several times a year. There’s an incredibly creative fashion community there. After 2014, the Maidan conflict, you saw a lot of creative energy coming from the region. Whenever there’s a political crisis or disaster, usually something comes of it. And a lot of creative kids came out of there.

The Soviet influence was also interesting. And the post-Soviet era, too. It’s this inoculation from the West and then all of these Western influences just kind of explode. It’s like when you finally get candy, you eat all the candy that you can. When I was living in Crimea, even in 2006, every single woman there was dressed to the nines, people walking around in full leopard print. To me, fashion is a portal into another world. It’s a form of escapism. It’s an outlet for you to construct a world that’s not your own, and make that world a reality.

The idea was to talk about clothes because clothes have always been a vehicle to the greater story.

I started #NeverWorns during the pandemic just to do something. It was all on Instagram Live, which everyone was doing, and the idea was to talk about clothes because clothes have always been a vehicle to the greater story. There’s a way to do it that leads you somewhere else. Honestly, I could probably learn everything about you through whatever shirt you’re wearing right now.

I was doing closet stuff for my former boss, Sally Singer, for a long time. And then I worked with Lynn Yaeger, and other people in the industry. It snowballed from there. I learned so many things while in these women’s closets—stories that I would’ve never heard face-to-face in the office, or even at a lunch. Even if someone says that they don’t care about fashion, you can learn a lot about them by what they hold onto and why they hold onto it. I was always fascinated by that.

You’re basically a therapist leading people to an answer that they already know. Sometimes, of course, because I worked at Vogue and stuff, people want me to tell them what to do. But ultimately, I’m just asking them questions to help them with a decision.

I think we made New York history with that sale.

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I ended up cleaning out Chloë Sevigny’s storage unit, and then also her closet. This was actually a conversation that started when I was still at Vogue. I was interviewing her for an article and I had done a closet sale with Sally and Lynn and Mickey a few months before. She was like, “You do this?” I was like, Oh my god, shit, maybe I shouldn’t have said that. But we started chatting and that was it.

I think we made New York history with that sale. It was a great experience, and I loved doing it but it was a lot. Not because of her, but the response online. I couldn’t sleep for a long time, and I think my immune system broke.

I’m actually writing a book about someone who cleans closets. I’m working with my former editor turned agent, Eve MacSweeney. It’s obviously based on me but it’s not really about me—it’s very fictionalized. It’s definitely more sexy than “how to clean.” We’re putting the finishing touches on it now, and I think I have to take a month off this summer from writing for any publications because I just really want to get it done.

I’m weirdly a thousand percent busier than I was when I was at Vogue.

I have a script I’m working on with a former colleague, and I’m doing a lot of #NeverWorns stuff. I’m in the middle of filming more episodes and editing them. Editing is a bitch, which I didn’t realize. I’m trying to figure out different ways to do these things. I’m taking meetings all the time. I’m weirdly a thousand percent busier than I was when I was at Vogue.

I think I’ve always had a scarcity complex. I catastrophize. I think, Oh my god, if I can’t make rent, this is it for me. I’m done. I once had a Russian landlord and while I lived there this other tenant went back to Uzbekistan and didn’t pay her rent. What happened in a month? The landlord took all of her shit and put it in the shed in the backyard.

So, I’m used to having this fear instilled in me. I have no other option than to make it work. And if I have to go back to being a hostess, I 100% would do it. I don’t mind.

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I definitely smoked weed in high school, but I swear to god, I think everything was laced with crack or something. There was something dangerous in whatever we were smoking because it was not normal.

I couldn’t smoke for the longest time because I would take one hit and all of a sudden my body would be freezing. I would be at my friend’s house and they would put 13 blankets on me. I would just be shivering underneath the blankets for hours or so paranoid that the cops were coming after us that I couldn’t relax. I couldn’t focus. Even in college, I passed out twice from weed. I passed out in the lunch line.

Now when I go out, I’ll have a beer, and that’ll do it for me.

I honestly don’t really drink anymore, either. I was actually sober for about two years solid. Now when I go out, I’ll have a beer, and that’ll do it for me. I can’t handle anything anymore, it’s really pathetic.

There was one night I got really, really drunk for no reason, and I just kind of stopped drinking. I was living in a windowless room in Bushwick, so I wasn’t sleeping well. My whole system was a wreck. I was overworking myself, exhausted, going out all the time, and didn’t want to be home. And what do you do when you go out? You drink.

So I just stopped. I started running more. I joined run clubs, and in order to join you have to hold yourself accountable. You can’t wake up hungover. You have to be up at 7:30 in the morning. And then when I tried to reintroduce alcohol, I couldn’t because my body couldn’t handle it.

I try to run every single morning for at least three miles. I have to do it. I think I probably have functioning low-grade depression and this is my Valium. It wakes me up.

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This interview has been edited and condensed for clarity. Liana Satenstein photographed by Meghan Marin in Brooklyn. If you like this Conversation, please feel free to share it with friends or enemies. Subscribe to our newsletter here.