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How Stella Bugbee's 'Twisty' Career Path Led Her to the Helm of New York Magazine's The Cut

From designing Broadway theater posters to becoming design director of "Domino" at just 30 years old, her upward trajectory was anything but normal.
Stella Bugbee in her office at The Cut. Photo: Whitney Bauck/Fashionista

Stella Bugbee in her office at The Cut. Photo: Whitney Bauck/Fashionista

In our long-running series, "How I'm Making It," we talk to people making a living in the fashion and beauty industries about how they broke in and found success.

You don't have to be an avid follower of the fashion or media businesses to know that they're both in dire straits. Aside from a recent wave of legendary magazine editors leaving their posts after decades on the job, the continuous game of designer musical chairs is more confusing than ever as labels desperately try to stay afloat — both financially and in terms of relevancy — in today's tepid retail climate. Though much of the industry is either stuck in an old-school mentality or following an outdated calendar, evolution is crucial for survival. Despite this hard truth, the fashion powers that be are notoriously resistant to adapt. 

One editor who's fervently embraced change is Stella Bugbee, the president and editor-in-chief of New York Magazine's The Cut. The women's lifestyle site (which also lives as a section inside the print issue) covers topics including politics, gender issues, the workplace, pop culture, beauty and, of course, fashion, with original photography, reporting and editorials, as well as fashion week criticism from Cathy Horyn and op-eds from the likes of Linda Wells, Allure's founding editor. Unlike many individuals in her position at the top of a masthead, Bugbee did not follow the "traditional" path to success, which generally involves interning, assisting and patiently working your way up the narrow, so-called career ladder with a specific goal or "dream job" in mind. Instead, she gained experience in a variety of fields, from advertising to design to teaching, before eventually becoming an editor.

Bugbee joined The Cut six years ago, and in that time she's become well-loved for her intellectual-yet-approachable method of covering women's interest topics, as well as her witty commentary on social media, her ability to find and foster great talents and her knack for all things visual. Although she's currently at the proverbial top, career-wise, she was met with some daunting personal and professional road blocks along the way that made her wonder whether she'd make anything of herself at all. Through receiving a frightening diagnosis, suddenly losing a job after a magazine folded and several periods of confidence-shaking lag time between gigs, she never stopped working, and her impressive portfolio of side projects ultimately helped her land to where she is today. 

At the start of fashion month, we visited Bugbee at her New York Magazine office to discuss her unconventional path to success, her transition from print to digital, the best career advice she's heard and why the industry is so desperately in need of change. Read on for highlights from our conversation.

Were you interested in or aware of fashion from a young age?

My grandmother worked at Bonwit Teller, which was the Barneys of Los Angeles in the '60s and '70s. She was a buyer for them and was really into fashion. On my other side, my grandma was a hairstylist. When we grew up, my parents had no money, so I lived between these two worlds of fancy grandparents and not-so-fancy parents. I remember very early on understanding that fashion was a form of social currency and that people who had money looked really different from people who didn't — and that people were treated very differently depending on where you were and based on what you wore. There's no value judgment there; it was just an observation that was obvious to me at an early age. My parents were friends with artists, photographers, actors and writers, so I also saw the power of fashion as a form of self-expression as opposed to a display of wealth. I was always fascinated with those two things: the way in which fashion and power overlap, and the way in which fashion and self-expression overlap. 

Did you always know you wanted to work in fashion and design? 

I loved fashion, but my parents did not think it was a valid thing to study or devote your life to. I was creative and wanted to go to art school. I went to Parsons, but it was never a question of whether I could major in fashion — I was not encouraged to do that. I was on the fence myself, so I ended up majoring in communication design. It was a marriage of all the things I liked: writing, visuals, photography, art direction, creative direction. I got to implement a lot of thoughts about style and design through that. I was really interested in publication design and the way magazines worked. I always knew I wanted to make a magazine someday — that was before the internet. 

When you were at Parsons, did you intern? 

I had amazing internships because I was in New York City. I worked for Roger Black, who designed every major magazine from Rolling Stone on upward. That was an incredible experience. I learned everything about the way magazines look and why they look the way they look. I basically worked seven days a week in college, either at my job or at my internship, and both were paid. 

How did you pay your dues and work your way up the ladder before you landed what you'd consider your first "big break?" 

I didn't have a clear trajectory the way that you would normally think about a graph and the line's going up. It was much more of a winding road. I graduated and I went to work for an advertising agency called Spot Co. that did all the theater posters for Broadway — we did "Chicago," we did "Rent," we did every major show — and it was super fun. I learned a ton, but then I got really sick. I have Crohn's disease and I got very ill, so I had to figure out how to change my life. I couldn't work 70 hours a week at that time. 

I quit and I started a company with two friends from college, and I started teaching at Parsons to supplement my income and get health insurance. We launched a small studio and we did identity work for galleries and museums and some video — a lot of web stuff. After that, we produced a magazine. [That] was so much fun, and I realized what I really wanted to be doing was editorial. I didn't know how to make the transition from creative direction into writing and editing, so I went to work for The New York Times Magazine as a freelancer because they had an opening in the art department. At that same moment, I started working with David Haskell on a project called Topic Magazine. It was all extracurricular time; I started working with him and another guy, who's a designer, and I realized that what I wanted to do was edit more than I even wanted to design — I really wanted to be thinking about assigning photography and the themes of the magazine. 

While I was at The New York Times freelancing, Adam Moss left and went [to New York] and I shelved my dreams for a minute again. I wasn't sure what I was going to do, so I went back to advertising. Most people in design pick a lane and they stick in it — you're either advertising-bound or you go into editorial and work your way up the magazine masthead. I was flailing. I was the design director at Ogilvy and we did campaigns for Coke, AT&T, Sprite and major corporations — then I got pregnant and I took 18 months off to deal with that. While I was pregnant, I was still grappling with being ill a lot. It was always about trying to find a way to work as hard as I wanted to work while coming to terms with being sick, and now I'm pregnant.

It's really intense to be sick in your early 20s because people don’t understand you — you're so different and in such a different place. I was not able to go out and party, and all my energy was spent on work. I was very motivated and extremely excited to do all this work. While I was out pregnant, I took on another magazine project. It was a quarterly with Joanna Goddard, before she was "Cup of Jo."

I was sitting in the sand box with my twins thinking I had to figure out my life, and Domino Magazine called. They asked, "Can you come in tomorrow to meet with Deborah [Needleman]?" I had no clothes; I had not been on a job interview in two years and I thought my life was pretty much over. I went to meet her and left the office building terrified, but also knowing that my life was going to change and it was going to make a major difference for us as a family. So, I took the design director job. I was 30.

Photo: Whitney Bauck/Fashionista

Photo: Whitney Bauck/Fashionista

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How did it feel to see Domino fold while you were there? 

It was incredibly traumatic. I had seven people in my department. For me, personally, it was not devastating, but it was very sad to see the ripple effect that it had on everybody who worked there. When they shut a magazine down at Condé Nast, it's not a kind experience — it's quite a roller coaster for people. I had been living the previous year as if I didn't have a job financially; I'd been saving because I was worried, and there had been other closings. It was really intense. I didn't have another job for months, and it was a rough year for [my family].

What wisdom about careers in general did you pick up from that experience? 

It was a very good lesson that you should try, whenever possible, not to accommodate to a certain salary, because that salary can be yanked away from you at any time. I had been comfortable at Condé, and then suddenly I had no Condé. It's also important to be thinking about what you want to be doing in five years — not necessarily where you want to be working, exactly, but just to have some vague outline, like, "I want to be freelance; I want to be the boss; I want to have a kid and work part-time; or I want to own my own company." If you have some idea of what you want to be doing, it makes all the bumps in the road easier to weather, because you [can see you're] still on the right path.

Did it change your perception of print media as a whole when that happened? Did you think, maybe, that wasn't something you were going to do again? 

It wasn't something I was going to bank on anymore. I wanted to get internet experience, and not be reliant on print. Then I got pregnant again, and truly thought that I wasn't going to do anything ever again. But that's the thing about pregnancy — if you're a very career-focused person, it can really mess with your confidence. It doesn't happen to everyone, but I've seen it happen a few times. I tell people that it's very important to believe in your own long-term ideals and not worry about six months [of leave]. Six months feels like a very long time when you're in the middle of not having a job, but in reality, in New York, people don't even notice when six months have gone by. 

How did you land at The Cut? 

I was on maternity leave doing nothing and trying to figure myself out at that point. David, whom I had done Topic Magazine with several years earlier, called me and said they were trying to find a person to relaunch The Cut. I met with Adam and Ben Williams and they asked me to do a memo; at the end of it, I took myself out of the running for the job and said I just wanted to consult. I had an eight-month old baby, but I really wanted to learn about the internet and I loved The Cut, I loved New York Magazine and I love Adam and Ben. I didn't know what it all meant and where it was all leading. Amy O'Dell was still here, and I helped them relaunch behind the scenes. When she left, it was time to make a decision, so I stayed and finally pivoted to being an editor. 

What was it like for you, working on the internet for the first time? 

It was a hardcore plunge in the deep end. I took to it right away — it was very fun to work with words, to make visual jokes, to go at that speed. It was different five years ago than it is now, but at that time, it felt like I was running a little marathon every day, and then start it all over again in the morning. I enjoyed that, before it was 24 hours, seven days a week. It has evolved. 

There's a certain fatigue developing that I see on Twitter and online — especially regarding the pace. But I don't think it's much different than any of the newspapers ever were. Some of the people that I work with now wrote for newspapers, and they have the natural inclination to be on this pace and be on schedule and they're great at it. Like Cathy Horyn — she is a natural writer for this medium because she thinks fast, files fast and is sharp in her assessments. Right off the bat, she comes up with these brilliant things to say, whereas people who come from a more long-lead print background have a harder time adjusting — they can, though, it's just a willingness to engage.

What's the best piece of career advice you've received that's stuck with you through the years?

I haven't received much career advice, but my husband — who owns a small design firm and has to hire a lot of people — often says: "You only do well in life if other people want you to do well." He must have said that to me 20 years ago when we met, but it's a thing I think about a lot; you need a community of people in order to succeed. Some think you can wing it on your own, but very few people do that, especially in New York. The framework and the network that you create is really important. [As is] being kind, because you never know. I have students that I taught at Parsons 15 or 20 years ago that are my colleagues, and my husband taught at Yale and his students hire him now. It's very important to consider yourself part of a larger whole and not think that you're going to make it alone. You should consider yourself part of a conversation and not the main person talking. 

What is the most pronounced change you've seen in the industry since you've been working in fashion? 

I've only been doing this for six years, but I think that the industry is more confused than it was when I first started. The hierarchy has broken down, and when that happens, it's hard for people to know who to follow, where to go and where to focus all their energy. The biggest change is that everyone is still operating under some old-school behaviors, while the literal firmament of our entire industry is crumbling and no one really knows how to cope with it. That's a true crisis. There are people doing it elegantly. There have been places like [Fashionista], Business of Fashion or [The Cut] who have navigated it better than others — only in the sense that they have taken [change] very seriously all along, so they are more prepared for it. There was more of a sense of certainty when I started, and now there's more comfort with uncertainty, because there just has to be. 

If you could tell your younger self something about the fashion industry that you know now then, but didn't, what would it be? 

I would say, you can be super-stylish without being super-skinny. I don't think that even occurred to me until recently — what a shame, all those years I spent thinking only certain people could be stylish. It would have been nice at that age to have a more comprehensive, inclusive idea of what style is the way that young girls have now. I think that is one of the most positive changes that I've even seen in the past five years. Diversity of size and race and gender is all so positive.

This interview has been edited and condensed for clarity.

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