Sally Singer: Guru

Kim Hastreiter // Photographed by The Selby

My longtime friend Sally Singer has always seemed to be a wonderfully odd duck in the field of fashion journalism. The super-smart editor and writer -- who began her career editing and writing about serious books for Farrar, Straus and Giroux and the London Review of Books -- was not the usual suspect for a career in fashion magazines. Yet that's where her passions have ultimately brought her. As a fashion-lover myself, who has often felt conflicted by the sometimes fickle and elite nature of the industry, I've always been impressed and amazed not only by Sally's lack of skepticism and her unwavering enthusiasm for the fashion universe, but also her belief that what one wears is not insignificant and can be a healthy means of self-expression directly connected to life in the real world. Only someone like Sally can culturally contextualize the style of the moment in a way that makes you think, "Hey, this is not silly stuff."

And she practices what she preaches, living her high-powered, working-mom life with gusto in her own eccentric off-the-grid style: Riding her bike to work everyday in her favorite YSL or Balenciaga; running to the emergency room on her way to a fashion show after one of her three cute sons gets hurt doing a skateboard stunt; ordering her weekly cruelty free organic food delivery from an upstate farm; searing duck breasts for a last-minute dinner party for 15 of her eclectic friends in her tiny kitchen in the Chelsea Hotel. It's also not surprising that she's been avidly reading PAPER for the past 23 years! 

After more than a decade at American Vogue as the fashion news and features director -- where she elevated the magazine with her writing, insights and intellect, lending big-gun credibility to smaller, young, alternative-thinking talents whom she consistently supported and fought to bring into the big glossy's fold -- Sally was recently hired as the new editor-in-chief of T: The New York Times Style Magazine. This makes so much sense to me. I can't wait to see how she'll bring her textured and quirky, democratic yet glamorous perspective (sans fear of being un-cool!) not only to their fashion but also design, food, travel and lifestyle coverage. We sat down for a great chat recently.

Kim Hastreiter:  After working for years as a book editor, your first job in fashion was at British Vogue 15 years ago. Was this a tipping point for your career?

Sally Singer:  My job there actually had nothing to do with fashion. I was hired to commission stories on culture, politics and society. But I also began writing style pieces for them. I'd always followed fashion, obsessively read fashion magazines, sewn my own clothes, followed all the credits and I always knew that I could cover the world of style the same way that I could follow the world of culture.
KH: After that, your fashion career escalated. You moved back to New York to be style director at Elle, then to New York magazine as fashion director and finally to Vogue, where you worked for almost 11 years.

SS: My job at these magazines was always about bridging the gap between features and fashion -- to make it clear that fashion is an expression of culture.

KH: Did you find that difficult to do? The fashion world is often a fairly narrow and not super integrated world.
SS: Fashion can be exceedingly insular and concerned with that which is visually new right now. The girl of the moment, the lip of the moment, the eyebrow of the moment, the hemline of the moment -- here today, gone tomorrow -- sometimes it seems a bit indulgent and decadent.  But at the end of the day, there is a way to speak to and excite many different audiences at whatever level they happen to be in the hierarchy of aesthetic-mindedness. There's a way to make the fashion universe realize that the world itself is interesting and stimulating. And there's a way to make the big world realize the show of fashion has relevance and that the visual stimulation that emerges from it is pretty cool, too. I thought about this all the time at Vogue. I'd say to Anna [Wintour], "Well, this is one for the fashion freaks, this is the one that's going to get  the industry excited, and this  is one for the reader." If in a shoot we didn't have something that made the fashion world, the stylists and the designers know we were at the top of our game, then we'd lost the lay reader.

KH: Design guru Dieter Rams always said that fashion is the antithesis of design. Because fashion is by nature something that is trendy -- its followers always long for that next big thing. Good design  is something that's long lasting. Why doesn't great, long-lasting design have  a prominent place in fashion?

SS: I think that great design certainly has a place in fashion -- look at the Levi's 501 or the Hermès "stud" watch. These are things that last in fashion. Whether they're part of the chatter or the song-and-dance of fashion, whether they were on the front page of fashion on any given day, might be questioned. But they certainly remain part of the fashion vocabulary. Things that are well designed can last, but fashion has to both be worn on a body and be relevant to its time moving through space. It's not like a sculpture that sits over there, and you can look at the lines and say that was really, really well designed. Fashion is about aesthetics and the zeitgeist.

KH: It's fierce, then it's tired.
SS: Or it's brilliant, but not cool at that moment. And the cool factor around things probably has to do with the zeitgeist. The chic-est, most beautifully crafted cocktail dress -- perhaps a [Geoffrey] Beene from the moment that Alber [Elbaz] was designing with him -- might be the best dress you  ever owned, yet there could be years when that would just not be the thing you picked to wear to a party.
KH: Because it's tired? Why?

SS: It's not tired. But for a while, it's just not part of the conversation of how you want to look, because of the music you're listening to, the book you're reading or the food you want to eat. You don't wear clothes in isolation. It might be the greatest thing ever, but it doesn't mean that every season, at every moment, you can work that look.

KH: Why can't you just be who you are? Is a bling-y person going to look wrong just because Jil Sander is the trend? What if the next big thing was suddenly  a hard-edged geometric Mugler style? I just couldn't imagine a casual, soft-looking person like you starting to wear architectural big shoulders, because that's not who you are. So why should we?

SS: No one says we should. People who are interested in style -- designers, stylists or the girl or boy on the street -- get an idea and fixate on it, and for their whole lives, that's their ideal. For someone from my generation­ -- West Coast, basically raised in the '70s -- my style ideal is probably a pair of jeans and a white T-shirt. Being very "done" or wearing a lot of makeup is very chic for others, but it will never be me. Yet every season, there's a way to connect your personal aesthetic with something new. You intuitively think, "I want something new that updates who I am, but at the end of the day I'm still myself."
      When people ask me what they should wear for evening, I say, "If you're most comfortable in your pajamas, then wear pajamas. Do not put on a ball gown, 'cause you're not going to look good in it." If your favorite thing is to wear party dresses because as a child every day you wanted to wear your fairy princess dress, then always wear fairy princess dresses. The smart person every season twists it just a little to register that they're part of the conversation. It's fun to update what is in your closet. That's why people who only wear pale blue button-front shirts, which I happen to love, buy new ones. They serially buy these things.
KH: Why would you buy a new one if you have ten in your closet?

SS: People think that if they buy classics -- a trench coat, or a V-neck sweater or a great pair of flat boots -- they're safe because they've invested in things that are gonna last 20 years. But within six months, it's the wrong V-neck or the wrong flat boot, because suddenly the line is wrong. Fashion people are stimulated by proportion shifting -- getting taller, getting thinner. Hemlines go up, hemlines go down. Shoes get wacky, shoes get clunky, shoes get skinny. The fastest things to date are those classics, cause it's just proportions laid bare. There's nothing else going on. If you had invested in a feathered chubby or an incredible crinoline, it's never going to go out of style. I think the most eccentric things are the things that last the longest.

KH: Fashion is also influenced by the sociopolitical -- things get humble, things get flashy. This is a good moment for someone like me right now, because being indie, grassroots and authentic is "on trend."  A few years ago, when the trends were more decadent -- pouring magnums of champagne on the floor for fun, driving Hummers or covering yourself in logos­ -- I didn't do well.

SS: It's all about the shapes the world takes.
KH: Will your new job as editor-in-chief of T be less about fashion with a capital F -- the hemline, eyebrow or lip of the moment -- and more about lifestyle, design, food, pop culture and travel?

SS: A lot of direction and change happens from fashion because every three months, four times a year, whether one likes it or not, there's a whole lot of new design that just goes out there. It might be repetitive, you might've seen it before, but I think fashion runs throughout everything. I don't think fashion exists in isolation. The bigger lifestyle shifts that everyone is adjusting to lately -- the needs to bicycle more, to consider locally grown food, to think about how we live with technology, which is a huge question -- are informing everything. Fashion is just what you put on to go out into the street to deal with all the other stuff. So everything has to be part of it.
KH: Do you see the New York Times as less elite than Vogue?

SS: I don't, because I don't think Vogue is elite. Vogue speaks to too many people on too many different levels. It has a very specific emotional connection to women whose mothers may have read it, whose grandmothers may have read it. The Times has a very similar emotional connection  to its readers, who read it to find out what's going on in the world and to come across as more literate, informed global citizens. T has to speak to that as well. So often people think that to be in the serious, journalistic world, that fashion and lifestyle are sort of indulgences that exist as a guilty pleasure. That's just utter nonsense to me. Everyone gets dressed every day and wants to look better. It's a common denominator. So the question is, what are you going  to put on and what is it going to say about you in the world?

KH: And what are you going to cook for breakfast?

SS: Yeah, and what are you going to buy at the grocery store or feed to your kids? Or how are you going to power your car?These are lifestyle choices that matter. They may not matter as much as other decisions you make, but these decisions are emotional and relevant. And they are, in aggregate, political.

KH: Many fashion players are not as political as you are. You've always voiced concern in this industry about ethics and human rights, supported underdogs and tried to help many of them. You've been one of those unique people in the fashion world who hasn't been afraid to think and act inclusively as opposed to exclusively.
SS: I just support the people who I think have talent and have courage in their convictions, regardless of the trends. Unlike a lot of people in the fashion world, I'm not afraid of being un-cool or of making images that aren't cool.

KH: I think it's a wonderful time for someone like you to be at the helm of a magazine to reshape it. What is Sally Singer's T magazine going to look like?

SS: I hope that there will be actual stories to read in it, because the Times is first and foremost a paper of great reporting. And it has to be relevant and honest and interesting. There also have to be real narratives and a sense of continuity between the world of the paper and the world in which the T images exist.
      To me, the most exquisite fashion credit I can remember in my lifetime was the day of [President Obama's] inauguration, when Michelle walked the parade route in that greenish-yellow Isabel Toledo dress. Because this was a real moment in which fashion, and quite directional fashion, played a role. When I think about the project of T and the Times, I think about that. I think about fashion outside of the studio and fashion that lives on the street. It doesn't mean you're going to repeat that moment, but I do think there's a way in which you can make lifestyle choices seem pertinent to the way we experience the world, and you can draw those connections in a magazine.
     You have to have many points of entry for readers on any page. From the person you shot, to the place you shot it in, to the context of the stuff, to what the stuff is, whether you have a political narrative, a celebrity narrative, a location narrative. Most people who read the Times are lucky enough to have some control over the choices in their lives. Those choices are emotional and about what moves you. If all goes well, the magazine I edit will feel emotional. It should feel like a friend or an enemy or an aggravating presence or the most wonderful thing you've ever had. Magazines, when they work, are emotional vehicles. They drive you to places you just didn't know you were going to go on the day you picked them up. And if they don't, they're not working at all.  

Subscribe to Get More