Former Editor-in-Chief and President of New York Magazine’s The Cut and current Styles Editor of The New York Times—Stella Bugbee joins to discuss her remarkable career in the media industry, covering fashion, beauty, and culture as a journalist, editor, and creative director.
Debbie Millman:
Stella Bugbee is the Style editor at The New York Times. How does one get to be the Style editor at The New York Times? Well, if you are Stella Bugbee, it has been a winding road through the world of New York media. Stella got her start in advertising, and later became the design director at Domino Magazine, just as print was getting overtaken by all things digital. She then led the relaunch of New York Magazine‘s The Cut, which became a wildly successful online style and culture site. Now at The Times, Stella joins me today to talk about her circuitous journey through the terrain of contemporary media. Stella Bugbee, welcome to Design Matters.
Stella Bugbee:
Hi, thanks for having me.
Debbie Millman:
Stella, I understand you were born in a giant mesa with no electricity or running water in New Mexico.
Stella Bugbee:
Yes.
Debbie Millman:
Why there?
Stella Bugbee:
They were living in Los Angeles, my parents, and looking to go back to the land. And my father tells a story that they rolled out a map of America and sort of looked for a spot that seemed remote and interesting. I did then go back and find a whole Earth catalog, I think it was from 1975.
Debbie Millman:
Great [inaudible 00:01:18].
Stella Bugbee:
That said, “You should move to New Mexico.” And I thought, “I wonder if it was really their idea or they were just responding to the zeitgeist.”
Debbie Millman:
They ended up moving to Washington DC, and then moved to Brooklyn as you went into fifth grade, I believe.
Stella Bugbee:
Sixth grade.
Debbie Millman:
Sixth grade. Sixth grade. But I understand you felt like a New Yorker well before that. When you found your spiritual resting place, standing outside Canal Jeans on Broadway. What happened when you did that?
Stella Bugbee:
So, my mom had met my stepdad while we were living in Washington, and we came to visit him and I was really into fashion. I don’t know what that even meant, but I was really into clothes. I was 10, and he took me to Canal Street outside of Canal Jeans, but there also used to be this incredible flea market on Broadway right across the street and also up the block, and there was antique boutique. And I had never seen such a concentration of youthful people dressed up in cool clothes and I thought, “I have to just live right here forever.”
Debbie Millman:
I felt the same way about the collection of stores right by Washington Square Park off of 8th Street.
Stella Bugbee:
All the shoe stores, yeah.
Debbie Millman:
Capezio, Reminiscence. And Reminiscence was my all time favorite store and I saved… My dad lived in Manhattan, my mom lived on Long Island with us, and I saved up to get a kind of not quite turquoise blue, a little bit more green in it, jeans and canvas shirt set.
Stella Bugbee:
Sounds good.
Debbie Millman:
So, there I was in these sort of turquoise-bluish-greenish jeans, the same color, short sleeve shirt and white Capezios. I just felt like that was it. There was no higher I could go fashion-wise.
Stella Bugbee:
The height to fashion for you. Yes.
Debbie Millman:
Yeah. You’ve written that you felt that you could carry the black and white striped bags stuffed with vintage clothes from Canal Jean up and down what you considered the Riviera of style, spanning Broadway from Canal to Houston. And that everything wrong in your life would be okay. What wasn’t okay at the time? Was it just being in sixth grade or parents getting divorced or…
Stella Bugbee:
I don’t know where to start. Yes, my parents were getting divorced. I am an only child. We had moved around a lot. I didn’t feel particularly settled. I had some substance abuse issues in my family. It was rough. I had a bit of a rough time early on, and there was something so soothing and escapist about seeing all this fashion and just kind of fitting in.
The other thing is that Washington DC, at that time, I don’t know what it’s like now, but it felt very financially segregated, I’ll just say. So, you kind of had to pick a lane and you had to stay in it, and it was very preppy. And even then I didn’t really particularly identify in that way, and I was just instantly felt like, “I’ll find some people here that will like me for the way I want to be.” And that was pretty obvious, just waltzing up and down that particular stretch of sidewalk. And at that point in New York, it felt really expressive. You just saw people walking around in wild outfits all the time.
Debbie Millman:
I really had this sense, as I was starting my research for today’s show, that you were a native New Yorker. And I went into my research thinking that, and then found out that no, you were born in New Mexico and then lived in Washington. I just had this sense that you were a true blue native New Yorker, as I am. But I’m glad that you’re honorary.
Stella Bugbee:
I think wherever you spend junior high school is who you are.
Debbie Millman:
I think that’s true too. Absolutely.
Stella Bugbee:
That’s so formative, that becomes you.
Debbie Millman:
Your grandmother worked at Bonwit Teller. For those that might not know or remember, was the Barneys of Los Angeles in the 1960s and ’70s. And your grandfather always carried around a beautiful Ralph Lauren bag, which I now know you carry.
Stella Bugbee:
Oh no, it was Vuitton.
Debbie Millman:
Oh, Vuitton.
Stella Bugbee:
Yeah.
Debbie Millman:
So interesting.
Stella Bugbee:
He loved Vuitton and he was very, very showy in a funny way, but also kind of dandy. I think what you’re remembering actually is a story I might’ve told you about carrying his Vuitton bag always to the Ralph Lauren show. He’s no longer with us, but I carry that bag in just as a kind of wink to myself and to him because I think he would’ve really enjoyed attending that show, so that’s my honor to him. But yeah, it’s beat up and destroyed, and I carry it anyway.
Debbie Millman:
When you were in high school, you and your poetry were featured in Sassy Magazine. How did Sassy discover your writing?
Stella Bugbee:
I had attended Bennington College’s summer program for writers, and I thought I was going to be a poet. I thought, really legitimately thought, that was going to be my life. And I had a teacher and she got me very involved in a program that worked with deaf poets, and we would translate each other’s poetry. And through that, I got into the New Rican poetry scene.
Debbie Millman:
Poetry Cafe. Yeah.
Stella Bugbee:
It’s quite a moment.
Debbie Millman:
Did you do slams?
Stella Bugbee:
I did. I wasn’t very good at them, but I did participate, and then I don’t actually know how Sassy came about, but I think somebody saw me there and they were doing a whole story about teenage poets. So, I was one of maybe three or four people featured. And I was very, very certain that that was my career. I was adamant.
Debbie Millman:
What kind of poetry were you writing?
Stella Bugbee:
Not very good poetry, actually. I mean, teenage poetry. I was really interested in poetry, actually. I think it’s still something I’m actually quite interested in and have become interested in anew, even in the last five years or so. And thinking about the way that poetry applies to what I’m doing now. I know that sounds really pretentious, but it does in terms of headlines and things like that. And I was just interested in forms. I got really into very technical, formal poetry, sestinas, things like that.
Debbie Millman:
You can send those to McSweeney’s. That’s the only poetry they accept.
Stella Bugbee:
Oh, really?
Debbie Millman:
Yeah.
Stella Bugbee:
Sestinas in particular, very hard form. But also, I loved concrete poetry, and I think that actually that’s what led me into thinking about typography, and was one of the reasons that I ended up choosing design when I ended up choosing design.
Debbie Millman:
Magazines were abundant in your house growing up, your parents had a subscription to Interview Magazine and Vogue, which you started reading when you were young. You also had a subscription of your own to Martha Stewart Living. What did you think of these magazines at the time?
Stella Bugbee:
I think that I’m someone who very much bought into the idea of aspirational lifestyle as a young child, and it was very real. You sort of felt like, “If I get Martha Stewart Living and I learn how to make cookies and make people happy and have a nice home, my life will be better.” And I think a lot of that did stem from the tumult of my earlier childhood and wanting stability and things like that.
But I really loved imagery. I think there’s something about the kind of imagery and the styling of editorial imagery that I bought into 100%. I really loved it. And whether it was Vogue or whether it was Interview, which was super cool, or whether it was Martha and food, and I don’t know, I wanted to live in those images.
Debbie Millman:
Did you have any favorite models at that time?
Stella Bugbee:
I didn’t. Models have never been the thing that interested me. I was always really interested in styling. I spent a lot of time thinking about Vogue and thinking about Old Vogue later on in my career.
Debbie Millman:
Grace Mirabella Vogue or Diana Vreeland?
Stella Bugbee:
No, Anna Vogue.
Debbie Millman:
Oh, Anna Vogue.
Stella Bugbee:
Because that was my Vogue. And I think she was really speaking to a kind of perfectionism that had a certain appeal to me at that time. The idea that you could be perfect, that you could aspire to be perfect. Now, of course, I know that that’s not true, but at the time it was alluring.
Debbie Millman:
I understand you really fell in love with design when you first saw Reagan Magazine. What intrigued you most about that, aside from the glorious typography and everything that was happening in that magazine?
Stella Bugbee:
I think it broke every rule. I was a first year art student at Parsons and trying to pick a major, and I could have gone any number of ways. I was really interested… and I was also studying writing at Eugene Lang, so I thought, “Well, do I want to be an illustrator?” That was really fun and briefly toyed with that.
But then there was such a magazine moment happening. It wasn’t just Reagan, it was Wired, it was wild. Wired was just doing the most experimental, interesting stuff with language. And I think, again, getting back to that concrete poetry side of things, I was fascinated by how far you could push language and still have it maintain readability, and what it felt like as a reader to be encountering language all blown up. And it just felt like this really experimental rule-breaking moment for typography, for language, for editorial, for creating a scene.
Debbie Millman:
Though you really loved fashion, your parents didn’t think it was a valid thing to study or to devote your life to. How come?
Stella Bugbee:
Yeah, I have said that before, but I think I would revise that. I think it just wasn’t part of our consciousness. It wasn’t that they actively would’ve said, “Don’t spend your time doing that.” It just-
Debbie Millman:
Well, if they were hippies, it might feel-
Stella Bugbee:
We didn’t know anybody who did that. They were school teachers, and came by life in a very different way and they were very literary. My mom has two MFAs in literature and it just wasn’t something that they thought it was a career in, exactly. They had no context for it, so they didn’t look down on it or something. Now that I’m a parent, I have a little more sympathy for where they were coming from. They were probably just totally unable to imagine what a person does in fashion.
Debbie Millman:
You mentioned that you went to Parsons as well as Eugene Lang, so you double majored in design and writing. Aside from poetry, what other kinds of things were you writing?
Stella Bugbee:
I initially thought I would study poetry and create writing as intensely as I studied the art. But what happened was I got into the art and I just fell in love with design, really and truly. It was like I didn’t know that a person could spend their whole life thinking about this stuff.
And once I realized that not only could you, but you could live doing that, you could make a living, it was like a real job. I kind of abandoned thinking about poetry because it felt so much less connected to what was happening in the world, and I just really wanted to be at the center of what was happening, and kind of in the center of culture. Though I loved the writing and the poetry, it felt much more niche to me at the time. So, I sort of abandoned it, to be honest. I didn’t end up graduating with the double degree. I only ended up with the BFA.
Debbie Millman:
You worked for Kate Spade when she and Andy Spade opened their first door on Thompson Street, and you said working there was a revelation. And when you were a sales girl at the original Hatbox size store, you felt like you’d been invited into a dreamed up world of creativity, an old-fashioned wholesomeness. I’m wondering what’s the biggest thing you learned from Kate Spade working for Kate and Andy?
Stella Bugbee:
Well, every detail mattered to them, and that was an important lesson. But also, you have to remember that in the ’90s, there was no internet. And so all your references, all your visual references, they came through hard work. You had to track them down, you had to accumulate a knowledge base that was yours. And they were so aesthetic and so knowledgeable and so tasteful, actually, in their own personal lives. And they were trying to take all of that knowledge and translate it into a brand, a fashion brand. And that was really cool to watch somebody do, and it was early days, small, tiny little store, and you didn’t really know what was going to come. I mean, now it all seems inevitable, but at the time it just felt very creative.
Debbie Millman:
Well, it was so different than anything else. There was so much context to the way they were creating their store and the aesthetic of their clothes and the whole Kate and Andy Spade experience.
Stella Bugbee:
I have so much more respect now even than I did at the time for how difficult it is to start a brand from scratch, especially a fashion brand, and have it resonate with people, and as quickly as that brand did. I mean, she had a background in editorial as well, and he had a background in design and advertising. And so I can look back on that and realize exactly the levers that they were pulling and all the tools they were using, and they had a ton of experience going into that building of that brand.
But it was not a sure thing. I mean, it’s an amazing endeavor to take on and have the confidence to try something like that. And then for it to succeed as wildly and as quickly as it did, just speaks to how sure-footed they were right out of the gate. And I think I got to see that up close and it was very natural to them. It seemed very natural to everybody who worked there.
Debbie Millman:
I’m glad that that brand still is around.
Stella Bugbee:
Yeah, and to see how it’s weathered these massive changes versus the small indie production that it was initially.
Debbie Millman:
You worked seven days a week when you were in college. You also had an internship with the legendary magazine designer, Roger Black, while you were at Parsons, and you worked on publications including Men’s Health and Reader’s Digest, and you said it was there that you learned graphic design was good training for decision-making. And I’m wondering if you can talk a little bit more about that.
Stella Bugbee:
Somebody was asking me the other day, “What did you like about art school? Why did you study design?” And I said that I thought a design education shows you how to solve problems. It shows you that there’s always more than one answer, and that freeing your mind up to have more than one answer for every single problem just makes you, I think, more empathetic to every problem that you’re trying to solve, and it makes you a better decision maker.
It’s like you have to make decisions really quickly sometimes, especially in editorial, and you have to sort of thought through all the other possible outcomes in order to make those decisions. I think design, really, it makes you realize you shouldn’t be too precious, I think. And working in magazines is very fast-paced, so you’re just making quick choices and then you’re onto the next magazine.
Debbie Millman:
And it’s also very subjective. There’s not only one answer to every question, but there are many that are really viable.
Stella Bugbee:
Totally. And that’s what I loved about the critique class process, and eventually I ended up teaching at Parsons, but I loved these classes where you would have a problem and everybody had the same problem and nobody had the same solution. And we had to, at that time, in those kind of classes, present three ideas and have valid reasoning behind why all three of them could work. And I saw that process play out in the actual workforce later on, but I treasure that lesson. I think it’s one of the most important things that design school, and all those internships and working at all those various magazines, taught me.
Debbie Millman:
Yeah, there’s something so interesting about going into a crit thinking your work is really solid, really good, feeling really proud of yourself and then see other people blow you away. And so you always have that, “What would that person have done?” And keeps you really striving, I think.
Stella Bugbee:
Yeah, and I think working on different magazines made me think about different audiences. And when you think about there being a different answer or a multitude of answers for any particular problem, it makes you think about solving the same problem. Let’s just say you’re basically solving the same problem for Reader’s Digest as you are for Men’s Health, but maybe for a totally different audience. So, how do you speak to what does the reader of Men’s Health need and how does the information you’re trying to design in that space speak to that reader? And how is it different than at…
Debbie Millman:
Yeah, especially with Reader’s Digest, which at the time had a bazillion subscribers. It always amazed me how many people read and subscribed to Reader’s Digest.
Stella Bugbee:
Yeah, it was wild. The other thing is, I didn’t care about either of those two publications, personally. I wasn’t invested in their content that I was working on, which I think was also a good lesson because I didn’t have to be necessarily to dissect them as problems to be solved. Right?
Debbie Millman:
Yeah. So, right out of college, you said that you got a job doing the exact thing you wanted to do, but within six months you realized you did not want to do that job, and so you called your mother and said, “I picked the wrong profession and it’s too late. Now I’m stuck for the rest of my life.” And she said, “Stella, you’re 22. You have plenty of time to change.” You disagreed and told her she didn’t understand that you had, at that time, invested so much in your career. You don’t have to tell us what the job was, but was that when you thought you should have gone to culinary school instead?
Stella Bugbee:
Well, let me be clear. I loved that job, and I loved those people and I loved that… It was really, I didn’t think I picked the right profession. It was not that any job would’ve been the right job for me.
Debbie Millman:
So, it was working in design.
Stella Bugbee:
Yeah, I was worried that being downstream from the decision-making process was upsetting to me at the time, which I’m sure is a relatable thing for a lot of young designers. And I knew even then, that the design part of it was only satisfying to me when I had some say, at least, in the content part of it, and I didn’t really know how to translate that into what… I didn’t know how to take all this stuff that I’d been doing, all this work I’d been doing, all these internships I’d had. And I loved design, but I didn’t really know how to solve that problem.
Debbie Millman:
Did you have that much confidence in design decision-making at that point to feel that you could do the bigger job?
Stella Bugbee:
I didn’t know what the bigger job was, so yes, I did. I had enough confidence to go start a company with my two colleagues and friends from college, so that I could have a little bit more control and be a little less downstream. I don’t know if that was confidence or just willfulness or what, but I-
Debbie Millman:
Drive, ambition.
Stella Bugbee:
Yeah, I think what you’re describing and what I called my mom to try to articulate, and not super successfully, was just that I wanted more control over what I was doing, and I was worried that I wasn’t going to get it for a long time in this profession. And I didn’t know how to fix that problem. I think that’s a conundrum that a lot of people come up against in design.
Debbie Millman:
Yeah, I briefly started a company, I believe I was 26 or 27, for much of the same reasons, but though I had the drive and the ambition, I didn’t have the experience. I mean, we did it and we did it fairly successfully for four or five years, but I was never proud of what we were making because I didn’t have the skills yet to understand how to make things that were better.
Stella Bugbee:
I absolutely ran up against a similar personal, sort of a lack of skills or just even experience in general. Wanting the control doesn’t mean you have the judgment yet. I knew that after that, even after doing that, even after trying to gain control over it, I actually had to go back into the workforce and get more experience and learn from others some more.
Debbie Millman:
Yeah. One of my favorite anecdotes that I read about you was when you were a very little girl, you went to a job fair and somebody asked you what you wanted to be when you grew up and you said, “In charge.” I could so relate.
Stella Bugbee:
There’s a pattern already. Yeah.
Debbie Millman:
So, you’ve had a number of really interesting jobs in that first decade of your career. You worked for Drew Hodges at SpotCo, the agency that does most of the theater campaigns for Broadway. I believe you worked on 52 campaigns that first year. You also freelanced at The New York Times Magazine. You worked at Ogilvy and Mather’s brand integration group and also began teaching, as you mentioned, at Parsons. You also worked at two independent magazines, Bene and Topic. Now, during this time, you also got really sick. Can you talk about your diagnosis and what happened after?
Stella Bugbee:
Yeah. I got sick right after college, and so that phone call that I made to my mom was also part of that. I thought, “I don’t know exactly how I’m going to work this hard, being sick.” I was diagnosed with Crohn’s disease. And so I spent a lot of years just trying to figure out how to balance the ambition that I had with the truth, which is that I was not feeling well, a lot of the time. That did affect a lot of decisions that I made, including the decision to have children earlier than I might’ve necessarily, had I not had Crohn’s disease. But other than that, I mean, I just trucked along. I wouldn’t say that I let it get me too down.
Debbie Millman:
You said that it was really intense to be sick in your early 20s because people didn’t understand you, that you were so different and in such a different place, you weren’t able to go out and party as much. How did you manage the ambition with the illness?
Stella Bugbee:
Well, also to be fair to other people, it’s not something I was talking about with anybody. So, if people didn’t understand, it’s also just not something that I was super open with it. It wasn’t something anybody was open with back then, I don’t think, as much as it is now. Now I meet people who tell me they have Crohn’s disease all the time. It’s sort of a common diagnosis. But back then I felt very embarrassed.
Debbie Millman:
Why?
Stella Bugbee:
I don’t know, because I didn’t want to be sick and I didn’t want that to define my life at all. In fact, I resented that it was there at all. You say, how did I balance it? I just didn’t really want to deal with it at all. Todd, my husband, Todd St. John, he’s also a designer. And sometimes we look back on that time in our lives and think, “Why didn’t we travel more? Why didn’t we do this or that?” But a lot of it, I think, was that there was work and then there was time where I needed to rest.
Debbie Millman:
Well, you also found yourself unexpectedly expecting twins when you were 28 years old, so that sort of changed everything.
Stella Bugbee:
Also [inaudible 00:25:40] on the travel. But I think he also worked really hard, and the two of us worked really hard in our 20s, and so we didn’t leave a lot of other time for socializing, especially if you count in the illness. There was a lot of time where after work I was tired.
Debbie Millman:
You ended up having to go on bedrest when you were pregnant. How were you feeling about where your career was going at that point?
Stella Bugbee:
I was not particularly hopeful at that point.
Debbie Millman:
I read that you thought it was a career apocalypse.
Stella Bugbee:
Yeah, I thought it was over. I thought my career was over. I didn’t really know what to expect, actually. And I think a lot of people I’ve spoken to feel that way on the cusp of their first child, of radical insecurity about whether or not they’re going to want to come back to the way that they had been working or whether they will be invited to come back into that pace. I, at the time, was working at Ogilvy, and it was really intense.
Debbie Millman:
Oh my God. I heard when Brian Collins used to bring in bags of donuts, it meant that everybody was staying overnight.
Stella Bugbee:
Yeah. I never stayed overnight, but I did eat a lot of candy late at night. Yes, I mean, I also really enjoyed that and I had incredible colleagues there and people that… I mean, for me, that was grad school, almost. It was an amazing experience, but it was very intense and not something you could go back to with Crohn’s disease and twins, clearly.
Debbie Millman:
Yeah, I look back at the pace that I had in my 20s and 30s and don’t know how I managed to stay alive. Actually, I look back on it now, I’m like, “How was that possible to stay up that night after night after night?”
Stella Bugbee:
Although it was really invigorating to work there, and David Israel and Weston Bingham and Alan Dye and…
Debbie Millman:
It’s a dream team.
Stella Bugbee:
And Brian was incredible. So, I just felt like I was in a very lucky place and I wouldn’t… If it took a lot, that’s what it took because I just wanted to be around those people.
Debbie Millman:
So, you then unexpectedly get pregnant. You’re on bedrest, you file for disability. You are considering the possibility that you’re in this career apocalypse, and there you are at 30, sitting in a sandbox with your two children, your twins, thinking you had to figure out your career, which you thought was pretty much over. And Domino Magazine calls you asking you to come in and meet with Deborah Needleman. What job did she end up offering you?
Stella Bugbee:
She needed a design director because Michele Outland was leaving, and I had thought to myself… I haven’t actually done editorial since college. I had done sort of independent projects, as you mentioned, but not at a high level. I really thought I needed to learn that. So, I was scared to go and meet with her, but we got along right away, and I loved the magazine. And I remember calling Todd and saying, “I think this is going to maybe be really hard, but it’s going to change our lives, and my life and I got to do it.” So, that was that. I started right away.
Debbie Millman:
You worked at Domino for three years and oversaw the design of every editorial page. You designed and directed the Domino Book of Decorating. You managed the art department, every aspect of the creative creation of the magazine. The magazine shut down and you left. And at that point, you got pregnant again. And at that point, you truly thought that you weren’t going to do anything ever again. Why?
Stella Bugbee:
When Domino shut down, that was a very insecure moment, I think, for everybody who worked there, and…
Debbie Millman:
It was just heartbreaking. It was such a great magazine.
Stella Bugbee:
Yeah. And it was very heartbreaking to see a whole entire staff get locked out all at once. That was sort of when I went to work in fashion for the first time. I went to work for Raul Martinez. That year that I spent working there, or a little more than a year actually, was my PhD. If Ogilvy was my master’s, then AR Media was a deep course in fashion and fashion photography and fashion branding. And I spent an entire year hanging out, reading Vogue magazines in their library, coming up with campaigns.
And so that was really a seminal, unexpected turn. It was back to branding, away from editorial, but it was… At that time, Raul was also going back to be the design director of Vogue. So, it felt like this perfect hybrid of the two worlds: branding and design and editorial, similar worlds, and fashion. And it was my first kind of real foray into the highest level of fashion.
And then I got pregnant, and then I thought I just… Every time a life change that happens, I think it’s very destabilizing. For me, it has been. Maybe some people are more prepared for things like that. I was not expecting that to happen, and I was a little destabilized and things were going great at AR. So, why did I think it was the end of my life? I didn’t see the path. I didn’t know. I think some people see their careers and their lives as a linear-
Debbie Millman:
Yeah, I don’t know anybody like that.
Stella Bugbee:
Yeah, I didn’t, and I couldn’t quite imagine what the next step would be.
Debbie Millman:
In an interview with Molly Fisher, she asked you if it was possible to be ambitious and happy, and you said you didn’t think so.
Stella Bugbee:
Yeah.
Debbie Millman:
Do you still feel that way?
Stella Bugbee:
I think that the last couple of years have been a real reckoning with ambition. Culturally, the whole culture has looked at what we think of as acceptable amount of hours to work, acceptable amount of time to spend with work, whether is work your family or is work, work. And we’ve thought a lot more about boundaries than I think we ever did when I was coming up in any of the professions that I got to work in. Yeah, I think I would revise that. Yeah, there’s a certain amount of misery that comes with ambition because you’re just always wanting something. You always want a little bit more.
Debbie Millman:
Yeah, you want more.
Stella Bugbee:
Whether you want it for yourself or you want it for the project or you want it for the world, that’s a good thing to always be striving to try to get something better or make something better, bring something out of a group of people. Whatever it is, may leave you a little wanting in the end you never quite achieve the ideal, but I’m trying to be both. I’m trying to be both happy and ambitious now.
Debbie Millman:
Same, same.
Stella Bugbee:
But I think culturally we’ve adjusted our expectations a little bit as a whole entire culture, and that’s been really interesting, and I think healthy and good, actually.
Debbie Millman:
I do too. I think there’s something really wonderful about the idea that you don’t have to go into the office every single day.
Stella Bugbee:
Yeah, or just like the horizon for what’s possible. When you have a pandemic or we had to shut down for so long, that had never happened in my lifetime, and it raised all these questions like, “Well, what is the horizon for success of anything, of a project, of a lifetime, of a relationship of a job?” If you have to put everything on hold for two years, well, that just stalls everything that you thought you were going to be doing, and maybe that was okay and it gives you a moment to reconsider what you should be thinking the horizon is for something. I don’t know if I’m making any sense, but-
Debbie Millman:
No, absolutely.
Stella Bugbee:
… that adjustment or the correction we are now in because of the ability to take that adjustment, I think was really one of the most important things that’s happened in my lifetime to the whole world. I can’t think of anything that’s had that big of an impact on how we think about time and how we spend it.
Debbie Millman:
During COVID, I remember… or during the roughest moments of COVID, I remember thinking, “I’m changing my life. I am going to do things differently. I’m having different priorities. I’m going to organize my time in a different way.” And that didn’t last.
Stella Bugbee:
What have you held onto?
Debbie Millman:
The desire to do it.
Stella Bugbee:
I feel a pretty profound change in that horizon. I think it’s okay to take a little bit longer to do things. It’s okay to be kinder to yourself and others about the time it takes to do things. And I think that’s helping balance that thing that you’re talking about is ambition and happiness.
Debbie Millman:
Yeah. Absolutely.
Stella Bugbee:
Because I think that that’s really the tension is the timeframe.
Debbie Millman:
Yeah. And I’m also aware of when I feel really happy, and it’s very rarely centered around achievement.
Stella Bugbee:
That’s good.
Debbie Millman:
Yeah. The knowledge is power, right? So, let’s talk about The Cut for a little bit. You started working at the New York Magazine‘s The Cut as a consultant in 2011. First to help relaunch New York Magazine‘s digital vertical, you ended up agreeing to join as the editorial director the next year. And in the 10 years you were there, you essentially reconstructed what was originally a Fashion Week blog and created a full-fledged magazine brand in its own right. What gave you the sense that you could do that, aside from just always wanting to be in charge?
Stella Bugbee:
Well, so New York Magazine has actually a precedent for a project like this, and that is Ms.
Debbie Millman:
Ms. Magazine.
Stella Bugbee:
And Adam Moss, who was the editor at New York Mag, I think that he thought there was space to push this, whatever he was calling, we were calling it a Women’s Vertical or whatever, into a vital internet publication. I stress the internet part of it because I think there was this permissiveness to give somebody, maybe untested, a chance, and that was the writers, that was the editors, that was the photo team. It wasn’t a whole bunch of experts coming in who’d already done a bunch of stuff. It was a bunch of young people. And we didn’t necessarily know exactly what the rules were, so that was good.
I’m not sure that I had the confidence necessarily to come in and do that, but there was a lot of interest in pushing things, and Adam was very experimental. And I had worked with David Haskell, who is now the editor-in-chief of the magazine on Topic, which was his project that you mentioned earlier. And when we worked on Topic, I remember thinking, “I just actually want to be picking the topic.”
It was Rob Giampietro and me and David. And while I was of course interested in the design, I was so much more interested in thinking about assigning stories for a specific topic, or picking the topic and then thinking about how to represent that. And so David, he knew that that’s sort of where my interests lay. Plus, I’d been working in fashion then for a year at that point before that, and it just was a strange job, and I had a strange resume, and it enabled me to pull upon everything I’d done up to that point.
It let me pull the branding and the art direction and the editorial ideas and put them all in one place, which lucky, so lucky, to be able to use all these weird experiences that didn’t necessarily add up to anything until that moment. So, it wasn’t necessarily that I had the confidence, just I had a really strange group of skills that applied in this particular instance, and then I ran at it, head on.
Debbie Millman:
I found this quote, something that Adam Moss said about you when he hired you, “The very unusual thing about Stella is that she has this big, important editorial job and has never been an editor before.” He went on to state that he, “Would’ve been unlikely to appoint a design director to run The Cut had he not already gotten to know you when you consulted.” And he stated, “What we saw then was that Stella was a natural editor with a crystal clear vision and incredible sense of story and great news judgment.”
Stella, what I love so much about this is that you succeeded by creating a magazine and a brand that you’ve described at various times as, “A smart, funny, clear-eyed look at fashion, beauty, and issues that matter most to women, that also blends a literary feeling with a punk feminist sensibility.” What could be better than that? How were you able to sell that and figure it out and then sell it in such a clear-eyed way? I mean, that’s what he said, in a clear-eyed way.
Stella Bugbee:
My main goal was to create a space where the people working on that project could say whatever they wanted to say, in the tone they wanted to say it in. So, it was always very much about the community. I used to make this arm motion where I put my arm kind of in a circle and I said, “I’m just keeping the space open so that we can do what we want and say what we want, and that we’re not being forced into a silo by some advertising category.” I think that’s really… if you look at most magazines, they were created for the purpose of advertising categories.
Debbie Millman:
And you created this for a certain sensibility, it feels like an attitude almost.
Stella Bugbee:
Yeah, psychographic, I’d say. But I firmly believe that there were people who wanted to talk about serious things and silly things at the same time in the same place, and that was fine. And I defended that urge more than anything. And it changed dramatically year over year over year. And so it wasn’t just that I had that vision from the beginning, it was sort of like, “Well, I got that done. What else can we do and how else can we grow? And who else can we bring on and what other voices can we put forth and what other challenges and ideas?”
And while that was all happening, the magazine was also feeding me incredible pieces. And I was working with the people who worked making the print magazine all the time and the editors on that. And I had an incredible partner in Lauren Kern who’s now at Apple News, and she was sort of my editorial partner on the magazine on the print side.
And once that came about, when she joined, I think that we all saw the real potential for it to be something very impactful. And again, we just all ran at it. For me, I didn’t want to squander that opportunity ever, at any moment. I thought, “What if no one ever gives me this opportunity again? I have to run at this.” And I wanted to give everybody else that sense that we got to run at this because we don’t know that this is a guarantee that we’ll always have a place to say and think and be ourselves, even with the precedent of Ms., having come out of that publication, which is really powerful. And I was operating a lot on other publications backs. I think you mentioned Mirabella, the actual Mirabella.
Debbie Millman:
Right. Grace’s magazine after Vogue.
Stella Bugbee:
Was an incredible magazine. Sassy. There was a precedent for some of what we were doing.
Debbie Millman:
Remember New York Woman?
Stella Bugbee:
New York Woman.
Debbie Millman:
Woman. Yeah.
Stella Bugbee:
New York Woman. Yeah, and in fact, I met with the editor of New York Woman early on in my time at The Cut because Pam Wasserstein knew her. And we went out for lunch. And it was important to me to note that we were part of a pretty healthy legacy actually, and we were just doing it on the internet for a new audience and building an audience in that space.
But a lot of people had tried to do what we were trying to do. And in fact, I have the very first issue of Mirabella, and I got it when we were relaunching The Cut in 2018 just as a kind of reference, and I couldn’t believe how contemporary it was and how it felt like it could literally be running now.
Debbie Millman:
Yeah. I want to talk about fashion a little bit.
Stella Bugbee:
I love fashion.
Debbie Millman:
You said that from the time you were little watching your grandmother at Bonwit Teller, you remember 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 they were treated very differently depending on what they wore. As a result, you’ve been fascinated with the way in which fashion and power overlap, and the way in which fashion and self-expression overlap. My question is, how have you incorporated expressing that fascination in the way you approach fashion and fashion journalism?
Stella Bugbee:
I think that a lot of fashion journalism is prescriptive, or at least it has been historically, and exclusionary. That’s why a lot of people have resentment toward fashion. They feel talked down to and excluded, whether it’s because they don’t fit in the clothes or they can’t afford the clothes or they’re for some reason excluded. It’s an industry and an art form that thrives on hierarchy and cast systems almost, and I don’t like that about it at all. I sort of reject that, and I kind of want everybody to feel like it’s something that they can and should embrace for themselves the way they would enjoy food or the way they would enjoy a great book or music, so that it’s a very personal, approachable part of your life.
And to go back to being in design school, for example, when I was in design school, I started seeing the world through design and it enriched my life. I got, “Oh, and this is why a chair looks the way it looks, and this is why Coca-Cola cans look the way they look.” And for me, fashion has that same thing. It’s like, “Well, you can choose to look however you want. Let’s think about that.”
And I would hope that certainly at The Cut, and perhaps less so at The Times, just because of what we’re doing at The Times, it’s very, very different. But I really wanted to start to open up a conversation for people and say, “You’re invited to this conversation if you want to be, on your own terms, and it’s fun, and you should want to cultivate a relationship to fashion and style for yourself, for your life.” Because it’s part of life, it’s really fun. So, a bit of taking away that power that fashion tends to have over people because it makes them feel excluded, that was important to me.
Debbie Millman:
One of the things that I’ve loved in quite a lot of your fashion coverage over the years is how you sort of democratize some of what we think about when we think about fashion, and also the range and the way that you put things together. But I really loved how obsessed you were for a little while there with Birkenstocks, and this was before Birkenstocks were back being Birkenstocks. And I’ve loved that you embrace both high and low at the same time. And it’s not just a matter of, “Here, we’re going to go high. Here, we’re going to go low.” You can match this up however way you want to, as long as you feel good and comfortable in whatever you’re doing.
Stella Bugbee:
I mean, I think one of the things that we were told… The magazines that I absorbed and loved so much that were so aspirational and exclusionary as a child didn’t always allow you to hold the complexity of the high and the low, of wanting to both talk about fashion and politics, of wanting to be able to indulge in something expensive, but also wear unique… Those complexities, those dichotomies, those contradictions are of life. It’s what everybody has inside of them.
And I think I was really interested in just letting all those things exist together. And I think that that’s when fashion becomes meaningful to people. One of the reasons why I cover the red carpet and what I think is interesting about, let’s say a red carpet event, is that’s where most people see the highest fashion come alive. It’s where they understand a gown. It’s not on a runway, and it’s not in their closet. It’s on their favorite star, whatever, movie star, musician, reality TV star, whomever it is.
And that’s a very fun space. I mean, it’s not stupid. It’s very fun. It’s very important that we think about the ways in which those intersections happen. So, I was very interested in collapsing some of the hierarchy around what was good and what was bad, what was high, what was low, what was accessible, what was off limits, and to whom. That’s really important.
Debbie Millman:
Is there a difference in covering a Met Gala versus going as a guest to the Met Gala?
Stella Bugbee:
Oh, sure, definitely.
Debbie Millman:
In what way?
Stella Bugbee:
Well, I’ve never been a guest at the Met Gala, to be clear. I mean, I think the most interesting thing for me about working at The New York Times is really thinking about those differences. What is the difference between covering? What is the objectivity that you bring as a reporter or an editor at The Times? How does that change your relationship to power, to the people in the room? How do you hold those people accountable when they’re not being honest? How do you-
Debbie Millman:
How do you? How do you do that?
Stella Bugbee:
By keeping yourself not a guest at the Met Gala. You have to be a little bit outside of that, and that’s the price that you have to pay. You get to sit in the room and enjoy some of those spoils, however you have objectivity.
Debbie Millman:
You see what’s really going on.
Stella Bugbee:
It’s a real… that kind of dynamic. Once you’re a guest at the table, you can’t be a journalist.
Debbie Millman:
How do you decide what you want to cover?
Stella Bugbee:
At The Times, the way the Style section works is sort of broken down roughly. We have a fashion team, we have a generalist team, so there’s news, there’s just stuff that’s happening. We got to cover this. It’s happening. And we try to set ambitious targets for that in terms of like, “Well, who’s interesting? Who do we think is pulling all the levers? Let’s go after that person in terms of let’s get a story about them. Let’s introduce them to a reader.”
And then there’s just like, “What is the reader interested in and what do we think is going to light their minds on fire? What do we think they’re going to share in their friend group chats?” That’s a big thought that’s always in my mind. And I don’t know, there’s also just a certain intangible instinct, and you never really know, but you just sort of develop over time, especially if you’re really looking at patterns over time of internet traffic. I mean, we have so much information available to us, and that’s the thing.
It’s like, “Well, you have to really read the tea leaves.” You start to think, “Well, why did that story do really well and not that one? And what’s the learning from that?” And not let that affect what you’re assigning too much, right? You have to think about what you think is interesting, what’s moving the conversation forward. And that’s the sensibility. That’s an intangible thing, actually.
Debbie Millman:
Before any publication went online, you didn’t know what people were necessarily interested in most. Yes, “Can this marriage be saved?” From Ladies Home Journal and so forth. But now, you know how many people are actually reading every single article that they’re reading and the direction that they’re going and so forth.
And in some ways, when you’re going through the paper, I still get the Sunday paper, you go through and there’s a lot of opportunity for discovery because you’re just seeing things as they pass by on the page. When you’re online, you tend to look for things like, “Thursday night into Friday morning, Modern Love will be up.” Social cues. You know when to find things, and you don’t have as much opportunity to discover unless you’re being fed, “You might also like this.” Which you have to then to decide whether or not you think it’s worth clicking. How much do stats actually matter to you? And I’m not talking about The Times. I’m just talking about you and your taste and what you believe should be published.
Stella Bugbee:
They don’t matter to me. I’m looking at them, I’m curious to see them, but I’m not going to not do a story that I believe in based on that at all. We came out of a decade, those of us who worked online, where a lot of decisions were made based on that, and I’m not sure that that was to the benefit of the content, always. And luckily, The Times really doesn’t dictate what we do in that way, which is really helpful. But I’ve developed certain instincts. I have a sense of, I think what’s going to be interesting to people and is there tension in the story? Is it a widely known subject matter? We just did a story about Barnes & Noble.
Debbie Millman:
I love that story and I love the images. It was so great to see all the different Barnes & Noble styles.
Stella Bugbee:
Well, that’s a design story, right? A total branding and design story. And several people on my team were very surprised at how big of a hit it was. But I knew it was going to be because I think there’s this huge interest in that brand, an innate interest in Barnes & Noble, why it’s not succeeding. I think actually people want it to succeed. So, what were they doing? And they’re doing something really weird, actually.
And I kind of thought, “That one will probably be a hit,” and you just develop instinct for what you think people will want to read. And I’m certainly not always right, by any means, but that’s kind of the way I use that information that I get every week, and actually every day, is just a sense of people really are interested in things that they already have emotional investment in. You write about Victoria’s Secret, people are going to read it. They’re curious about that brand, regardless of what you say about it. So, there’s certain topics that you sort of recognize will be interesting.
Debbie Millman:
You’ve written that, “Runway show going requires stamina.” Is that because of the pace?
Stella Bugbee:
Yeah, there are people who just love going to fashion shows, and I think they’re really interesting, especially if that’s your beat and that’s what you cover. But the grind of going to maybe 50 in a row, especially if you’re a visual person, you have to pace yourself. It’s a lot of images, if you’re thinking about it that way. I mean, sure, experiencing that just on Instagram when I’m not, let’s say I’m not in… I didn’t go to Milan or something. I’m experiencing it as a reader and as a viewer, it’s a lot to watch other people experience it. Imagine being there. It’s a lot of images.
Debbie Millman:
How do you feel about your own fashion when you’re watching shows or in the midst of the fashionistas?
Stella Bugbee:
Probably like most people, I have a fraught relationship with fashion. If we’re talking about what I wish I could have versus what I have. But this season, I tried a different approach, which was while I was walking around and going to shows, I started keeping a list on my phone of reminders of things that I actually like so that I wouldn’t lose sight of my own desires and my own taste, just to remind myself, “You know what? You really like this and you really like this.” And this is a hard-won, decades-long project to develop what you actually like. Don’t be too swayed just because everything is shiny.
And that’s a different approach than I’ve taken in the past, and I think that that’s been healthier. Because otherwise, you can get very wrapped up, very quickly, in kind of the dizzying aspect of all of this new, beautiful luxury, very distorted reality, which most people… I don’t think most people change their fashion every six months.
Debbie Millman:
Well, it’s just that in technology that have that sort of forced obsolescence embedded in it, which is so hard to manage emotionally because you want to sort of be stylish or in style or have the latest, greatest whatever. But that’s a lot of pressure, it’s a lot of money, it’s a lot of consumption.
Stella Bugbee:
I mean, the real hardcore fashion is for the very young, who change their fashion all the time and are trying to figure out who they are and are using style as a tool to do that, or the very wealthy, who can afford to do that. For the vast majority of us…
Debbie Millman:
And the very skinny.
Stella Bugbee:
Yes, the body that can handle that kind of change and can afford to handle that kind of change. The vast majority of us will buy a coat in 1990. I’m looking at you. I know-
Debbie Millman:
Oopsie.
Stella Bugbee:
I know you still have a coat that I admire from 1990, and keep it, right? And so how do you bridge that continuity of self year over year? That’s not something that you can sustain changing all the time, most of us. So, then you have to develop your own personal taste, which I think gets back to my goal for all of us, which is cultivate your own taste, have confidence in what you like, make your list, “This is what I actually like,” so that you’re not feeling swayed all the time or insufficient because you can’t participate for whatever reason: money, age, body, any of those reasons. It helps to have a strong foundation and understand what you actually like. And then I think you should just totally lean into that. No trends, nothing. Find yourself and enjoy yourself with fashion. That’s my main goal in life.
Debbie Millman:
Just have fun with it?
Stella Bugbee:
Is to divorce it of its power over our minds and to gain some control over that and say, “I really love this.” I love it the way I love this couch that I bought 25 years ago, and I keep recovering this couch. Well, you know what? I love this coat I bought in 1990 and I’m going to keep wearing it. I think that that’s really important, both for the Earth, for our minds, and for some semblance of control over that industry.
Debbie Millman:
You said that we can’t fix how anybody feels about their body, but we can disabuse people of the idea that certain styles are only for certain people. Do you think that designers are really paying more attention to that now?
Stella Bugbee:
There was a moment where I think we saw this little window open up and it seemed like that was going to be a priority. I’ve actually seen incredible backsliding in the last couple of years. This season was abysmal for body inclusivity. You’ll have one or two people in each show. And some brands are doing great, I should say that. But then I think with the introduction of Ozempic, it’s like everybody just gave up. I don’t know. I mean, it felt very-
Debbie Millman:
[inaudible 00:57:29] that way.
Stella Bugbee:
Yeah, it felt like market changed all of a sudden. And fashion is cyclical, and it’s not that deep, as we would like it to be. So, some of these changes that were kind of promising and exciting, we’ll see if they stick.
Debbie Millman:
Well, you had a lot of ability to help reframe the way people think about style and beauty and size at The Cut. Do you feel you’re able to do that at The Times as well?
Stella Bugbee:
The Times project is super different.
Debbie Millman:
In what way?
Stella Bugbee:
Well, it’s not a luxury sales project. We’re not making fashion shoots. We’re not really telling people what to buy so much. I mean, there’s Wirecutter, but we’re not a luxury fashion magazine. We’re a news organization. We’re part of a news organization. I don’t see my role as sorting through and telling people what to purchase. Even our critic, Vanessa Friedman, she’s not doing that. We’re not doing that. We’re taking what’s happening and we’re explaining it to people, but we’re not saying, “Here’s the 10 greatest coats you can buy right now.” That is not part of the project. So, it’s really different, and I don’t really even see that as part of my job as much as it is to document what’s happening in fashion right now.
Debbie Millman:
Right. As we’ve been talking, I realized what it was that I loved so much about your leadership at The Cut, which was I never came away from reading The Cut feeling bad about myself. And I’m not really in the same position when I’m reading The Times because it is more journalistic and it’s not as whimsical, I guess. But I hope that your voice can come through those pages as you continue to work there.
Stella Bugbee:
Well, I would certainly hope that you would never read the Style section and feel worse for wanting to know about any of that information. That’s important. And to treat the subject matter seriously, I think that’s a big important characteristic of the Style section is that we take it as seriously as anybody takes anything that they do there. But we also still have a lot of fun.
I wouldn’t want anyone to come away reading one of our stories, feeling worse about themselves or bad for wanting to know about it. And I think a lot of what we do actually is give people permission to enjoy the stuff that we’re covering. And within the context of The New York Times, that’s pretty important because there’s a lot of very serious, gut-wrenching stuff that happens in the sections other than mine. And that’s okay to then turn to us and enjoy yourself over here. I think it’s really important to say, “It’s okay. It’s okay. Come on over here and enjoy yourself.
Debbie Millman:
Yeah. So, this is my last question. You’ve had a long, illustrious, circuitous career, but you’ve also had some painful, harder times, and you’ve written about how when you look back, it looks like it was intentional, but you’re old enough now to admit that that was not the case. It seems like it was premeditated, but it was all accidents the whole time.
I think that’s really helpful for people to hear as they’re navigating their own ambition and their own career paths. It seemed like at the time, you had no idea whether you would recover from the various obstacles in your path. How do you think you were able to overcome those obstacles and what has it taught you about control?
Stella Bugbee:
Yeah, I have said that I felt like it was an accident, but actually one of the things I’ve been thinking a lot about in the last couple of years is that I looked at all these things as opportunities. So, they felt accidental or they felt like unexpected, is maybe a better word, but I was always able to look at each opportunity or each experience and say, “Well, this will complete a little puzzle piece that I’m missing. I don’t know about fashion, not really, not at the level that Raul Martinez knows about it. What can I get by working with Raul Martinez? That’s the highest level, he’s really good at it. What will I learn from this man?”
And it wasn’t necessarily clear to me what I would do with that, but I knew that it would give me this critical piece of knowledge and a way of looking at the world. And the same for Adam, and the same for Drew Hodges. I saw these people and these opportunities not necessarily in a connected way that was obvious at the time, but that they each offered opportunity for growth and to complete a sort of thing I was lacking.
And so I think that’s how, in retrospect, it makes more sense to me. It’s like, “Well…” And I would hope that that’s still the case. I still sort of think of that. I look at these incredible colleagues that I have and these people at The Times who’ve worked there for 35 years and who just know so much. And I think like, “Well, what does it feel like to put myself next to the people in this room and what can I learn from them?” That’s how it’s made sense.
It’s less that, “Oh, it’s all been accidental and oops, here I landed here.” It’s more that if you see an opportunity or if you are given any opportunity, find the little core inside there that’s going to give you the most knowledge that you can then take and apply to something else, or try to find the thing within any experience that completes a missing part of your education.
Debbie Millman:
Stella Bugbee, thank you so much for making so much work that matters. And thank you for joining me today on Design Matters.
Stella Bugbee:
Thank you for having me.
Debbie Millman:
Absolutely.
Stella Bugbee:
It’s been a pleasure.
Debbie Millman:
To see more about what’s Stella does, all you need to do is read the Style section of The New York Times. This is the 18th year we’ve been podcasting Design Matters, and I’d like to thank you for listening. And remember, we can talk about making a difference, we could make a difference, or we can do both. I’m Debbie Millman, and I look forward to talking with you again soon.