Anna Wintour on Politics and the Fashion Business in Trump's America

There is no one in the fashion world quite as powerful — or as polarising — as Anna Wintour, the American Vogue editor- in-chief. This year, she is tasked with steering the magazine through its 125th anniversary amidst a political, economic and technological disruption that is shaking the very foundations of the global fashion industry over which she has ruled like a head of state for almost 30 years.

In part one of the cover story from BoF's latest special print edition (available to order here), Imran Amed sits down with the most powerful figure in fashion to pick her brain about the future of the industry, the future of magazines — and even the future of Wintour herself, as she prepares for the Met Ball, plans her next issue and contemplates what 2017 may bring for the business of fashion in America and beyond.

Read part two of the cover story: Anna Wintour on the Met Ball, the Future of Magazines and Her Own Future

NEW YORK, United States — "I kind of call her the chairman or president of the fashion industry," says Bob Sauerberg, chief executive of Condé Nast, when asked about Anna Wintour, the editor-in-chief of American Vogue and artistic director of the storied media giant that owns it. "She plays a role and advises everybody, including us. Yes, she's our creative head, but she's also a terrific business person."

Indeed, Wintour’s role is much bigger than Condé Nast and her influence is felt far beyond the company’s New York headquarters. She is an unofficial, behind-the-scenes consultant to CEOs, designers, politicians and movie stars in America and beyond. She advises major European luxury conglomerates like Kering and LVMH on new designer appointments and chairs regular breakfasts discussing the season’s most important fashion trends with the head honchos at American luxury department store behemoth Neiman Marcus. Designers seek her advice on potential investors; and investors turn to her for tips on the hottest new design talents.

A small sampling of her itinerary during the last round of fashion weeks demonstrates just how deeply she is embedded in every corner of the fashion industry and its intersections with politics, celebrity, pop culture and the arts.

There she was in New York alongside Hillary Clinton — the candidate she vociferously supported during the 2016 US presidential election campaign — at the unveiling of a new postage stamp honouring the legacy of their mutual friend, the late designer Oscar de la Renta. There she was again in front of Milan's Duomo before the memorial service for her friend and longtime Vogue Italia editor Franca Sozzani, walking hand-in-hand with Sozzani's son, Francesco Carozzini, who, just a few days before my interview announced his engagement to Wintour's daughter, Bee Shaffer.

Wintour with Alex Bolen, Michael Bloomberg, Hillary Clinton, Janice Walker and Anderson
Cooper at the Oscar de la Renta stamp unveiling | Source: BFA/REX/Shutterstock

In Paris, she posed with model-of-the-moment Gigi Hadid and her heart-throb pop star boyfriend Zayn Malik at a cocktail party for the finalists of the 2017 edition of the CFDA/Vogue Fashion Fund. A few days later she appeared at a press conference with the reclusive designer Rei Kawakubo of Comme des Garçons, the subject of this year's Metropolitan Museum of Art Costume Institute exhibition, an annual institution which Wintour has transformed into a global media platform whose opening night fundraising gala has been called "the Superbowl of fashion."

Sauerberg is right. Wintour is indeed more like a head of state than a mere editor-in-chief, a position which gives her a unique, bird’s-eye view of the fashion industry, emanating outwards from Vogue and Condé Nast to the wider ecosystem that sustains this $2.4 trillion industry. So who better to talk to about the disruption striking the very core of the American fashion business than the industry’s most valued advisor and de facto president?

It’s 8:34 am on a crisp March morning and Wintour is wearing Prada. She welcomes me warmly into her office and we sit down at the famous Alan Buchsbaum desk that has appeared in countless photographs and films. True to reputation, there is one lipstick stained Starbucks cup front and centre, as well as an array of Apple gadgets: an iPhone, an iPad and a MacBook Air.

Behind her, on a silver serving tray sitting on a sideboard, sits a stack of recent issues of American Vogue, including the 800-page September 2016 issue, featuring cover star Kendall Jenner. American Vogue's September issue remains the most important issue of the most important fashion magazine in the world. But these days Vogue's September issue carries fewer ad pages than it once did, reflecting the wider decline of print advertising. (The biggest-ever September issue, featuring Lady Gaga and weighing 4.5 pounds, with a total of 916 pages — 658 of them ad pages — was published in 2012.)

In response, Wintour and Sauerberg have implemented a raft of operational and organisational changes to position the company for a leaner and meaner digital age, including several rounds of layoffs; shuttering Details, Self and Lucky magazines; making Teen Vogue a digital-first publication with only four print issues; folding Style.com into a new “Runway” section on the Vogue website; and bringing all of the company’s 21 creative teams — encompassing magazines, websites and Condé Nast’s creative agency 23 Stories — together under a new corporate creative director, Raúl Martinez.

I’m here to understand what the most powerful figure in fashion makes of the chaos unfolding around her: a traditional media company trying to reinvent itself for the digital present; a fashion industry in rapid flux; and, perhaps most of all, a country that has found itself governed by a hugely controversial president whose economic, foreign and social policy positions veer unpredictably from one pole to another. From her perch in the offices of the now 125-year old American Vogue, with its headquarters at the politically charged address of One World Trade Center, Wintour, too, is grappling with what Donald Trump will mean for America — and the world.

Imran Amed: What do you think Vogue stood for back in 1892 when it was founded, and how has that changed?

Anna Wintour: Well, I wasn’t around in 1892, believe it or not! But Vogue was a society magazine. It reflects the time in as much as fashion reflects the time. I think that whatever you see on the runways or on the streets, in a movie, on your Instagram feed, whatever it may be, fashion can tell you what’s going on in the world.

Sometimes you need a little bit of distance to understand what it might be. For instance, I was so moved by the [women’s] marches that I asked our features department to find somebody who had actually marched in the ’60s. They found a wonderful writer called Mary Gordon. She had to sneak out of the house, not tell her mother, not tell anybody and go and march, and then sneak back into the house and her family never knew. This time of course, mothers, daughters, grandmothers, boyfriends, husbands, whatever — everybody was marching together. So it was interesting to see how much the world has changed.

And also, looking at what was worn then and what is worn now. To me, fashion is ceaselessly fascinating because it is an expression of self. And whatever year you might be looking at in Vogue, that’s what we’re trying to do — reflect the time, reflect the moment. Whether it’s through fashion photography or through our political coverage or our cultural coverage, a magazine is a living, breathing thing. You need to be of the moment, not too far ahead, not too far behind. You have to reflect what one sees happening.

I can't recall a time that has been as full of change, but I also can't recall a time that's been as fascinating.

IA: Can you recall a time when you’ve had to reflect such a turbulent period though, in terms of the political environment and technology and everything that is changing the world?

AW: Well it’s an overused word, but disruption is the word that you go back to. One of the initiatives I have here in my role as artistic director is that I have regular Editorial Task Force meetings, or ETFs, where we invite leaders from other worlds to come in and talk to the editors-in-chief and the digital leaders and a few other people about what they see happening in their industries, whether it be media or Silicon Valley — we pull them from everywhere.

One overwhelming message, particularly from Silicon Valley, is that you can’t be frightened of change. A traditional company is the most difficult to pivot and you have to be open to new ideas and not be worried about failure. I think when things are challenging and different, it’s actually also a very exciting time, because it does give you a freedom to try different things. I found the discussions that we’ve had over the past two or three years so helpful and so interesting, because I do find, especially since we moved down to this building [away from the cultural life of New York], that you get a little insular and caught up in your own world and doing things a little bit too much the same way. So when you open up the conversation to people who see things completely differently, it’s very inspiring.

IA: Yes, this morning, I was watching your speech at the Oxford Union. You said: “This is the problem of very long established companies, they tend to get set in their ways. I’ll be the first to admit that at Condé Nast we have been guilty of arrogance — we are Condé Nast, we have always done it this way. We are so busy working at being the best, being perfect, that we haven’t always been open to disruption. I hope that’s changing.” Is it really changing?

AW: I think it has. I mean it’s really completely reshaping how we do business, how we look at things, how we can be much better partners to everybody that we work with. We are a media company and we reach audiences in ways that we have never done before. It’s absolutely extraordinary the breadth of who we talk to — and in so many different ways, and how interesting that is, and how the news cycle has completely changed — whatever way you’re communicating. So the opportunities are thrilling, they’re daunting too at times, but they’re also thrilling.

So yes, I can’t recall a time that has been as full of change, but I also can’t recall a time that’s been as fascinating. You had the piece on diversity — and it’s certainly something that we’ve talked about a great deal at Condé Nast, and certainly here at Vogue, inclusivity — and we have to reflect the world that we live in. I think fashion, and I count us within that too, has been guilty of being too narrow minded, and thank god that’s changing. I think it’s wonderful.

IA: But don’t you get frustrated sometimes? Your March issue, which had all those amazing women on the cover was making a specific effort to be reflecting a more inclusive view...

AW: It wasn’t the first time. We did a whole issue last January on diversity.

IA: But still the feedback — and you get instant feedback — and people say, “Oh, well this has been Photoshopped and it’s not diverse enough,” etcetera.

AW: And it wasn’t Photoshopped! What you learn over the years working here is that we’re always talked about and sometimes it’s great and sometimes you’d be amazed what people focus on. But you know where your heart is and what the editors and the photographers and what everybody here is trying to do, and that’s what you have to stand by. If you worry about every little tiny criticism, you won’t get up in the morning. It just comes with the territory.

IA: So in this environment with all of this change, what elements of the traditional magazine do you want to keep and what do you want to do away with?

AW: We know that our audience comes to us for the best. They remain engaged and involved and tell us what they feel and what they think — and to me that is the best reward. You can’t chase the clicks, you can’t chase the fast buck. You have to stand up for what you believe in and that’s what everybody here at Condé Nast believes.

IA: You talk about not chasing clicks, but if I look on the Vogue.com site and I look at Vogue the magazine, there’s clearly a different tone and a different approach to the way Vogue manifests itself digitally. And I’m just wondering how your teams work together. You’re all in one place?

AW: We’re totally integrated here on one floor. It’s total integration and we meet, we discuss, we talk all the time.

IA: Do you go on the website every day and look at everything?

AW: I do. I do. But I feel it’s — you have the opportunity today to talk to your audiences in so many different ways. We talk to them through the work that we do on the Fashion Fund, we talk to them through the books that we publish, we talk to them through our videos. We talk to them through the work that we do at The Metropolitan Museum, through our Instagram feed — whatever it may be. So it shouldn’t be homogenised. Yes it’s all about quality and authority and doing what we all do at Vogue, but each one requires a slightly different way of discussing or addressing the audience that you’re talking to.

You also can’t control everything and nor should one want to. The joy I think about having all these different opportunities to talk to different audiences is that everyone that works on them constantly surprises and delights and informs what I do. I like to know what’s going on and am aware, but I’m not a micro-manager. I don’t feel people work the best way under those circumstances — if they feel someone is always watching every single thing. So we try to encourage in everything we do for all the different editors and writers and photographers to take ownership and feel good about what they’re doing.

IA: One of the things that the rise of digital has done is that it has shifted the focus onto people at the shows. There are all of these editors that have become part of the landscape of fashion in a way that didn’t exist before. What do you make of it all?

AW: I think that pretty much anything that gets people, audiences excited about fashion, interested in fashion and following the personalities that are involved is great. I look at the streetstyle pictures that are on our site and many other sites and I find them very, very inspiring and fun — and thank god they’re not all dressed in black the way they used to be. I like seeing people making such an effort and having so much fun with it.

We were talking just the other day for a story we’re hoping Grace [Coddington] will shoot on the creativity of chaos. We got that idea most strongly from Miuccia [Prada’s] runway show, where it showed everything all sort of jumbled up and looking like it came from different countries and different identities. That’s what I’m inspired about when I see the streetstyle, when I see someone who doesn’t look like they came straight from the runway, who’s actually put it together with their own personal style and invention and humour and wit. I think it’s fabulous, why not? It gives you something else to look at when you’re waiting for the show to start.

British prime minister Theresa May in American Vogue | Photo: Annie Leibovitz

IA: Going back to something you said earlier — if fashion reflects the time, then it’s hard to think about the current times without thinking about politics.

AW: Did you just come from London?

IA: I did.

AW: Did you see our Theresa May coverage?

IA: Yes, actually, I took some pictures. It was on the front page of every newspaper. It was kind of incredible.

AW: Yes, for some reason they had the idea that we might be putting the prime minister on the cover. That was never part of the discussion, and I don’t know where that came from. I was concerned that they might be disappointed.

IA: Well they weren’t. It was everywhere — a political story in Vogue. I was doing some reading and learned that Lee Miller, Vogue’s war correspondent at the end of WWII, actually published some quite provocative photos on the topic of the Holocaust — so in a way, Vogue has always addressed serious topics like politics.

AW: Yes, we do have a history. I never understand why no one has made a movie about her, because she’s such a fascinating character. Thank you for looking at that. It was shocking at the time, or maybe shocking isn’t the right word.

IA: Arresting?

AW: It was arresting and stunning and remarkable that Alex Liberman, who was the editorial director at the time and who was really one of my great mentors, he had the fearlessness and the compassion and the humanity to see how moving and emotional those pictures would be.

IA: When thinking about the Theresa May story — why do you think the American Vogue reader is interested in that?

AW: I think they’re interested in women and— going back to our 125th — that’s really what we decided to focus on throughout the year. Rather than just one issue, we thought we would just look at women in all different walks of life. Going back to Vogue having that sense of responsibility to reflect the time, that a woman is prime minister in Britain, which is our great ally, for the first time since Margaret Thatcher. We know that our readers are interested in politics, we know they’re interested in women, we know they’re interested in the world, so of course, she was a natural fit for us.

IA: The environment here in the US is also so politically charged at the moment. You supported a very different presidential candidate quite vocally. It’s not even been 100 days yet, but what do you personally make of it?

AW: I think we’re too close really to understand what the impact is going to be and what indeed is going to happen. There’s almost too much news. I don’t know what you see. I see everybody had been — or still to a certain degree is — so hyper-engaged in the Trump presidency and he gave them so many reasons to be engaged and it was almost like you were looking every morning just to see what had been said, or what might happen. I feel now that people are accepting it a little bit more, it’s becoming — I don’t want to say normal — but they realise this is just the state of play.

Now is the time when we need to really start to assess what it’s going to be. Because I think it’s been so much, so fast and so incredibly different from what many of us have believed the direction that this country might go. I think it was very, very hard to really understand and process. I feel that it is calming down a little bit and now is the time when we really do need to see what we can do and how we can be helpful to the causes we believe in.

Actually Diane [von Furstenberg] has a great quote in the March issue — there’s no point about whining or complaining or screaming. The country voted. So what can we do now to be most helpful and to also stand up for what we believe in? People can have disagreements. They feel equally strongly about what they think is right as we do about [what we think] is right. So let’s try — to use a well-worn phrase — to reach across the aisle and see what we can do to work together. I really believe that — because just dissent is not enough.

IA: Is that why you held those meetings with President Trump? I think people were quite surprised.

AW: Well I have known Donald Trump, I think, since the early ’80s. Anyone who was out and about in New York — and he was out and about in New York — [would know him]. Ivanka has had a long history with the magazine, and I have respect for Ivanka and everything that she has achieved. And, as I mentioned to you before, we have these ETFs where we invite outside people to come in and talk to us about their vision and what they see — and so obviously it made complete sense to invite the then-president elect to come in and talk to all of us here. We’re a huge media company. I believe he also went to the New York Times. I think it was a very natural thing for us to do.

It made complete sense to invite the then-president elect to come in and talk to all of us here. We're a huge media company ... It was a very natural thing for us to do.

IA: Some of the policies that are being touted by the Trump administration — especially the import tax — are worrying for the fashion business.

AW: I don’t think we have clarity on that. He has said many things, but what can he actually achieve? There are a lot of checks and balances along the way. I think there’s been a lot of noise and now is a time for assessment.

IA: And then there’s the complicated issue about how Vogue should cover Melania Trump. Vogue has for a very long time covered first ladies. Helen Taft was one of the first people featured in the magazine and Hillary Clinton was the first first lady to be on the cover. Is that a tradition that you’ll continue?

AW: We always photograph or cover in some way the first ladies, so as I’ve said before, I can’t imagine that we wouldn’t at some point cover the first lady, but we’ve got nothing planned right now.

IA: Do you see that as part of the responsibility of Vogue, to cover someone who represents the current administration?

AW: Yes and I think we have to respect the Office of the President of the United States of America and I think we also need to respect different points of view. It doesn’t mean that we are necessarily agreeing with everything that they say, but a lot of the country does.

IA: Since you started here at Vogue, how do you think the business of fashion in the United States has changed?

AW: Well, I think it used to be that the American fashion landscape was made up of some very dominant brands. Whether that was Calvin, Ralph, Donna, Michael and Marc — they were really household names and to grow and become anything close to that was a 10-year exercise. What I see happening now is that it is so much easier today for young talent to emerge and be recognised and to find a customer. If you are talented and you use a modern way to communicate and you do all the things that you need to do, you can be established so much more quickly.

It’s also incredible how sophisticated the customer is and how much they know and how they don’t want to be taken advantage of — even a customer who has time and is privileged and has money and can spend a lot on clothes. They will price out something online and not want to be taken advantage of and I think that’s a huge, huge change.

IA: Your role in the fashion industry goes far beyond your role here. Some people see you as a consultant or an advisor or a consigliere — even a secret whisperer — to help the cogs of the industry move. How did that first happen, that you became so involved?

AW: I think it’s part of the joy and the responsibility of this job. Vogue is the pinnacle in terms of representing the fashion industry and I think it honestly goes with the territory and it’s not something that is just me — we all do it. Sally [Singer], Virginia [Smith], Mark [Holgate] — we’re all out and about, talking, listening, trying to help. I think it benefits everybody, it helps us and it helps others.

IA: How does it help you?

AW: I think it makes our jobs clearer. We need to understand not just our side of things, we need to understand what’s happening in the retail environment, what’s happening in terms of the different brands, what the audience is telling us, what their customers are telling us — it informs all of us.

IA: But how do you respond when people say you’re the most powerful figure in fashion and that the whole industry works based on what you say?

AW: It simply isn’t true. It simply isn’t true. I love my job, I love everything about it. I love the additional responsibility that I have as artistic director and I love journalism. My dad was an editor, my brother is a political editor, it is just a world that I am steeped in. And honestly without sounding pretentious, I don’t think about power or what that brings me. What does that really bring? A good table at a restaurant? I just try to use my position to help Condé Nast and to help others.

IA: Then why do you think that myth has developed around you?

AW: I can’t answer that.

And with that, my first interview ends. I have a second interview with Wintour scheduled for a couple of weeks later — partially because, I am told, she doesn’t like long meetings and also because I have plenty of topics still to discuss. That morning, news breaks that Edward Enninful has been appointed editor of British Vogue, a position that Wintour herself held for a short stint between 1986 and 1987. Wintour is also busy preparing for the “Met Ball,” the Costume Institute exhibition’s opening night fundraising gala, that is to take place on May 1st.

Read part two of the cover story: Anna Wintour on the Met Ball, the Future of Magazines and Her Own Future

This article appears in BoF's latest special print edition: "America." 

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