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How Leah Chernikoff Went from Studying for the LSAT to Running

This is one full-circle "How I'm Making It."
Photo: Tyler Joe

Photo: Tyler Joe

Break out the bubbly: This January, Fashionista turns 10! We know, we can hardly believe it ourselves. To celebrate the place where so many of us got our start in the industry, we'll be taking a look back on all the things that make Fashionista one of our favorite fashion sites out there (not that we're biased!). Today, we're catching up with Leah Chernikoff, Fashionista's sixth editor and the current editorial director of 

Leah Chernikoff brought me on to intern at Fashionista all the way back in 2012 because I commented obsessively on the website, where I eventually learned enough about how to be a fashion writer on the internet that she hired me on full time. I start with that fact because I would bet I'm not the only fashion writer out there who owes their career to Chernikoff, who has a knack for finding talented people. It's the skill of someone who started her own career in journalism after discovering she had a passion for good storytelling from unexpected places — including herself. Just 10 years ago, she was thinking about attending law school .

"I was studying for the LSATs, because I thought, well, I guess I'll just go to law school now. But I just didn't want to do that, and the LSATs are awful, so I didn't even take them," she says. "I got this little scholarship to the Salt Institute for Documentary Studies, and then that led me down a path of media and storytelling."

I chatted with Chernikoff at Hearst Tower in the offices of, which she joined after Fashionista in 2013, and where she currently leads the charge in delivering stories on everything from the Women's March to Kylie Jenner's newest lip kit. It was funny to be interviewing her for our "How I'm Making It" series, not just because she was my boss, but also because she's the one who came up with the idea for the franchise in the first place. Sometimes, things just come full circle like that. Read on to hear why Chernikoff's first job was a failure — in a good way! — and why sometimes your friends can be the best mentors. 

What about fashion interested you?

It's funny, because I fell into it a little bit. I always loved looking through fashion magazines and I always loved getting dressed up, but I was never someone who could ID any model or knew what season that designer look came from. Steff Yotka will always know what Marc Jacobs collection something is from; that was never me. When I got my first job in journalism at the Daily News [in 2007], I was in the features department and they didn't know what to do with me because I was new. It was fashion week, and they were busy, so they just sent me to fashion shows and I was like, "This is great!" Then I just kept doing that.

What had you done before Fashionista?

I went to Bowdoin, a liberal arts school, and I majored in English literature, so I think in some ways that prepared me for writing and editing and thinking critically, but I had no idea what I wanted to do. It was a wonderful experience, but they don't necessarily set you up for a career; it's more about critical thinking and a well-rounded education. Then I got out and I was like, 'Oh, shit!' I had done one internship in college with a nonprofit educational organization and I luckily managed to get a job there.

I read a lot of Gawker at the time, which was around 2004. It was very personality-driven and there were a bunch of really smart, funny writers on the site then. I also used to listen to a lot of NPR and many of the stories I listened to were produced by Story Corps. I was like, well, this seems like a great job, making stories and telling other people's stories. I looked at the Story Corps "About Staff" page, and all of them had gone to this documentary program called the Salt Institute for Documentary Studies. It gave me a break where I could get some clips and learn about writing, listening and storytelling. 

Then I came back to New York with no job and just hustled a lot until I got one. My first little-known job was at a Bauer publication, Cocktail, [a] weekly magazine. It folded before it launched, but I met a lot of great people there that continue to be mentors and collaborators throughout my time in this industry, so it was a really important and great first step. It was also a very realistic welcome to the world of journalism in New York: You have a job for two weeks! Five people started the day they told everyone it was shutting down.

Why did you want to work at Fashionista?

What appealed to me was the voice, that it was personality-driven. It was digital-native, and at the time I was at the Daily News; there had been rounds and rounds of buyouts — of course, many more would follow, like at any major newspaper — but I was like, I have to figure out what the digital world looks like and exist in it. I saw Britt [Aboutaleb]'s goodbye post and I reached out. Somehow, that all worked out; Lauren [Sherman] liked me.

What was that experience like?

We were in a little apartment building with one room and little desks for each site: Above the Law, Dealbreaker and the sales team. I think Moby lived in that building — it was on Mott Street. Everyone was kind of shout-y; if you imagined a small media startup, I think that's what you would picture. Lauren was very patient with me because I had to get my speed up. But it was fun; you just had ideas and then you did them. I was like, "Oh, this is just how it works, that's great!"

How were you finding stories and getting access to things at the time?

That was one of my biggest worries coming to Fashionista: When I pick up the phone, everyone understands what the Daily News is, and everyone in New York wants to be in the Daily News. If I pick up the phone and say I'm calling from Fashionista, is anyone going to take me seriously? But I used the reporting skills that I had learned and honed at the News and people responded. I think we really built up — and continued to build up — the credibility over the years. It was about creating relationships and nurturing them, proving that we were serious and did real reporting.

How did you come up with the "How I'm Making It" franchise?

It was the first franchise I ever thought I should do when I started at Fashionista. I always felt the Fashionista reader wanted to figure out how to get into fashion — any sort of aspect of it — so I thought it would be a good platform for promoting new talent, but also letting readers get a glimpse into the nuts and bolts of how someone actually got from here to here.

What was your goal when Lauren Sherman left and you got the job heading everything up at Fashionista?

I probably should have had one coming in, but I was just like, "What is this new world I'm stepping into?" I don't know that I had a really clear one, other than that I wanted to do reporting. I wanted to bring those skills to a website. I felt that, even if it wasn't true that blogs didn't do reporting, there was a stereotype that they didn't, so I wanted to push against that and prove that wasn't going to always be the case. But I did love that you could have an opinion, and have a voice and engage with a community of readers. We grew in staff and also in site size, like areas of coverage.

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Ruthie Friedlander, Britt Aboutaleb, Leah Chernikoff, Hayley Phelan and Lauren Sherman at Chernikoff's wedding. Photo: courtesy of Leah Chernikoff

Ruthie Friedlander, Britt Aboutaleb, Leah Chernikoff, Hayley Phelan and Lauren Sherman at Chernikoff's wedding. Photo: courtesy of Leah Chernikoff

What were you looking for in people that you hired?

I will use you as an example, because I could tell from the comments that you were incredibly engaged and passionate. I could tell that you already got it; it's like you already had a head start. I was just looking for people who were smart, and really, really invested and interested in the site. At that time, you could get story ideas from the comments, or you could find people that you wanted to hire from the comments, because people were thoughtfully engaged and had opinions that would maybe prompt a follow-up post. If someone will get the tone and the speed and really love the site — I don't know if there's anything other than that, than being smart and creative. A sense of humor was always really key for me too, because it's only fashion! I think it's important to maintain a sense of humor about it. You were able to be silly, too, which was very important to me — I hope it made it somewhat fun.

When did you know that it was time to leave?

I think when I had started feeling too comfortable leaving every day at a normal time. I'm a little masochistic in that way, if I stop feeling like I'm always needing to be doing something. I could have been like, "Hey, you've got the hang of this thing now!" but instead I was like, "Okay, I need to throw myself into something where I'm drowning again."

What was appealing about Elle?

It was a brand that I'd always really loved. To me, it always proved that being intellectual and curious and engaged, and really liking fashion and beauty, none of those things were exclusive from each other. I felt like Elle always struck a really nice balance of: You can read an article — a really in-depth and well-reported political profile — and you can find out what black boots you want to buy. That was what really appealed to me, because at Fashionista it's just fashion. At the Daily News, I'd covered features more broadly, and I really wanted to be able to have the chance again to cover areas that were not strictly fashion anymore.

How did learning digital at Fashionista help with this job?

Well, I think I was recruited because I was at Fashionista, so I think I owe everything to that experience. I think Troy Young, who is the president of Hearst Digital, wouldn't have come to me if I hadn't had that experience at Fashionista, and hadn't been able to grow the team and the site there. I understood speed and got to understand voice. I got to understand really listening to an audience, being respectful of them and engaging with them rather than just sort of dictating. I think that's the beauty and the danger of the internet — you hear back all the time.

How have you seen the digital landscape change?

I don't know if I can even answer that! It's changed so much, it's crazy; I can barely sum it up. At the beginning of Fashionista, it was fun and we were growing the site, but I think the analytics have changed digital enormously. You have so much data on what everyone's reading, how long they're reading it for. Social media has changed everything. That's the biggest thing.

How do you view your own social media?

I probably should care about it more than I do! I think it's really valuable, and I admire and respect the people who are able to build a following around their own names, but I'm a bit social media shy. Twitter is terrifying! I'm on social media constantly, because that's the way we reach our readers, that's the way content — which is a word I hate — surfaces. It consumes everything for better or for worse — lately, for worse. So I'm always in it, I'm just not putting my own stuff into it. I'm thinking more about the brand and what we're putting out.

What would you say your goal is for

There's an essay Chimamanda Ngozi Adichie wrote for Elle that was in print right when I arrived, in which she describes her journey to embracing style in a work environment (for her, the western academic world) that frowned upon it. She puts it far more eloquently: "Women who wanted to be taken seriously were supposed to substantiate their seriousness with a studied indifference to appearance." She concludes, of course, that it's possible and even necessary to embrace personal style and be intellectually curious and excel at one's career. That's the ethos that I try to apply to to create a space that embraces, considers, and questions style, politics, beauty, culture, relationships, celebrity, humor, knowing that these are all things that our readers are interested in. 

How important have the relationships you made through Fashionista been to you on a professional level? 

[Former Fashionista editors and I have] all supported each other since we met, and Britt and I never even overlapped. They're some of my best friends; they all came to my wedding and we have supported each other in friendship and careers along the way. It's really one of the most amazing and special things about that place. Everyone's such a nice, good person. Women are just told, "If you find a mentor, you'll be set," but that never happens. Or if it does, it doesn't happen the way it seems it will. They're often the people who are your best friends right next to you, so I think that's really been special.

What is your ultimate goal professionally?

I don't know yet! The thing that always keeps me moving forward is to be telling interesting stories and being able to be a platform for new voices, too. So as long as I'm doing something that's involved in telling stories that I think are engaging and worthwhile and might otherwise not be heard, then I'll be satisfied. 

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This interview has been edited and condensed for clarity.