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How I Broke into Fashion | US Vogue's Sally Singer

Sally Singer went from literary publishing to editing features at US Vogue, before helping to spearhead a major digital drive for the Condé Nast title. How did she do it?
(L-R) Andre Leon Talley, Sally Singer and Grace Codington | Source: Getty Images
  • Kati Chitrakorn

There are few sectors of the economy that offer as wide and interesting a range of career opportunities as fashion. "How I Broke Into Fashion" offers a first-hand account of how top fashion professionals built their careers in the industry, tracing their path to success. For industry advice or more jobs like this, visit BoF Careers.

NEW YORK, United States — Currently the creative digital director of American Vogue, Sally Singer has a long history of working in magazines. She began her career at the London Review of Books and British Vogue. After moving to New York City, Singer joined American Vogue in 1999, initially as fashion news director, then as fashion features director.

In 2010, she went to T: The New York Times Style Magazine and spent two years as editor-in-chief, before returning to the Condé Nast title at which she has spent a majority of her career. Two years later, Singer was appointed as American Vogue’s digital creative director and is tasked with harnessing the full potential of, having overseen the launch of

BoF: What attracted you to work in fashion media?

SS: I was always interested in fashion. I was certainly obsessed with it as a child, but I never thought I was going to work at a fashion magazine. In fact, it never occurred to me that I could work in fashion professionally. When I was young, I sewed my own clothes and based my ideas on what I saw in Vogue magazine, making my own personal interpretation of brands like Calvin Klein.

I learned a lot from my mother, who always emphasised that every garment had to be as good on the inside as on the outside. I learned about technical terms like dirndl skirt and gore. The thing is you don't really know what something is — or appreciate what a good one is — until you've tried to make it yourself.

I was also a huge club kid. That was a very important part of my life, to be able to go out and hear music, to go to clubs and create personas at night. I do think that a lot of people who are successful in fashion come out of that inventive world of nightlife. Everything magical happens after nine at night.

BoF: How did you develop your early career in fashion publishing? And how did those experiences lead to Vogue?

SS: When I lived in San Francisco, I worked for a woman who was an antique dealer and had a store called “La Vie Du Soleil” and I was a salesperson there. During that year I also worked at a very over the top Jewish delicatessen. Those were my first jobs after college.

Then I went to graduate school. When I left, my first job was at a travel magazine start-up called “Travel Holiday,” which was later bought by the Reader’s Digest Association. [The title was later sold to Hachette Filipacchi Media US and ultimately closed in 2003].

I learned a huge amount about publishing when the magazine’s relaunch took place. I learned about how covers were picked, which fonts to use, the way you do a listicle, how to approach an infographic, how to edit — there was so much talent in such a strange little magazine. But the reality is that I was a waitress for most nights in New York. I actually earned money as a waitress for years.

I later got a job and worked at a literary magazine called the London Review of Books. By this point I really wanted a job at Condé Nast and was very fortunate to be hired by Alexandra Schulman at British Vogue, who had the imagination to think that someone like me could work on her magazine. She also had the courage to let me do a lot of style pieces, even though I had been hired as a commissioning editor for features.

BoF: After 11 years at Vogue in an editorial leadership role, why did you transition to digital? What opportunity did you see?

SS: I left Vogue around 2010 and joined The New York Times, where I became editor of T: The New York Times Style Magazine. That was a huge project in itself and it was also the first time I worked on digital content, where I had to think about what works in digital and what works in print. Later on, when I returned to American Vogue, Anna [Wintour] said to me: “The website is what you should do next. You should work on something purely digital.”

At that time, I realised was a beautiful and faithful representation of the print magazine, but it was a terrible website in terms of UX, UI and any sort of digital capabilities. So I set out to work on it. It also led to the birth of our Instagram account and today we’re almost at 65 million followers across all our accounts, including Vogue Runway and Vogue Beauty. There are stories that are great in print, others are better suited online, and then there are some ideas that can run across all of Vogue. It’s a lot of content, and a lot of negotiation.

I don't have any social media accounts myself. A lot of people think that if they have a big following on Twitter or Instagram, then they’re digital and that defines them — it’s as if being your own brand is the point of being online. That’s not true for me. I may work in digital, but my life is offline. It allows me to work more clinically. My role is focused on growing Vogue’s presence digitally and creating a [digital] foundation for the brand as it moves forward.

Fashion's not just about who's in or who's out. You need a profound curiosity about 'the now.'

BoF: How did you approach the role and adopt new technical skills?

SS: When you work with really good people, you ask questions and you listen. If you think about online and social platforms, it’s just a tool. How do you play with that tool, and how do you take it to a place it hasn’t been yet? Where do you go next? Those are the things I’m interested in. If you work that way, you slowly figure it out.

I think there are some things you make because you want to achieve scale and hit big numbers. But there are other things that you do, because you want to touch the right audience, in the right way. Some of the collections we cover on Vogue Runway are never going to be top performers online, but they’re for the people who need that news on that day. We also cover topics that are very broad because there may be people looking at it who don’t even realise they’re reading Vogue. They just want that information.

BoF: How are Vogue’s audiences changing and how is the publication reflecting that digitally?

SS: The audience for is no different to the audience in print. We know this from the analytics we see — they’re not younger, they’re not better educated, they’re not richer or poorer and they’re just as interested in fashion and shopping. It’s not as if there are big differences in the profile of the person.

I think that the print reader’s connection to Vogue tends to be historic and emotional. They’re looking for importance and legacy, the composition of the images and writing is what attracts our print readers. Online, people are looking for all sorts of things. People want to be amazed and informed — they’re looking to be provoked, inspired and activated to do something.

We have a digital team that works on and they cover the things they’re obsessed with, or interested in, and what intuitively feels right and relevant. We have a writer who obsessively covers the Eastern European landscape in fashion, and another who is obsessed with models. Every single person on the team has a personality — and that’s encouraged.

BoF: Tell me about a favourite project and the lessons of success you took away?

SS: This is Vogue’s 125th year, so we’re trying to do very special projects. Some of my favourite photo shoots have been with diverse communities in America. We did a whole series in March on “The American Woman,” chronicling the lives of women we found interesting in this country. That was very important for me to do this year, because it’s proof that we don’t live in a bubble.

We wanted to see America. We wanted women from the Midwest, rodeo queens and sorority sisters who went to historically black colleges. We wanted to show the diversity and beauty of women of all ages. We were looking for people and trying to understand this country at a very strong turn in terms of electoral results.

This month we launched the Celine Dion couture shoot and it's the first time we did an exclusively digital editorial shoot. We managed to put out online two or three different experiences with Celine Dion. In print, it would have just been one shoot with one story attached to it. We've also not filmed couture like that before. We've done the collections, but never couture.

BoF: What do you think is essential to being successful in the fashion industry?

SS: It's good to be a sponge and be interested in what things look like and feel like. You have to be intensely curious and receptive to all the aesthetic influences in the world that you can possibly pick up. You also need to have lots of stories that you feel like you've been dying to tell your whole life. Fashion's not just about who's in or who's out, or what you look like or what you can afford. You need a profound curiosity about "the now" and be able to connect that with something far more timeless.

This interview has been edited and condensed.

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