David Remnick: When it was announced in June that Anna Wintour would step back from her role as editor-in-chief of Vogue, the flagship US Edition, it wasn't one of those items that's old news in a day. Speculation, analysis and commentary circulated all summer, but now Wintour has named her successor, Chloe Malle, who's worked at the magazine since 2011.

Now, I'm hardly an objective observer here. Anna and I have been colleagues and friends for a very long time. Even as Chloe Malle takes over at Vogue, Anna will remain in very senior roles. She's the Editorial Director of all the Vogue editions throughout the world, and she's the Chief Content Officer of Condé Nast, which publishes The New Yorker as well, but what's unique about this particular change of the guard is that Wintour is synonymous with Vogue itself.

Many people these days can't name the editor of a major newspaper any more than they can name the King of Belgium, but when the camera pans to Anna Wintour in the stands of at the US Open or Wimbledon, you know who that is. No chiron necessary. Wintour was appointed creative director of Vogue in 1983, then editor-in-chief in 1988, and whole generations of designers have come up under her famously decisive judgments. She organizes the Annual Met Gala, which she grew from a charity dinner into a global phenomenon. We met in our studios at One World Trade Center.

Anna Wintour: Here I am, a lamb to the slaughter.

David Remnick: That's exactly what's going to happen. How are you?

Anna Wintour: Good.

David Remnick: Anna, we are talking on the day that Condé Nast announced that Chloe Malle is going to succeed you as editor of American Vogue. How do you feel?

Anna Wintour: I feel great. I love Chloe. I'm very happy for her. She's going to do a brilliant job. We've worked together for well over a decade, but at the same time, she really had to prove herself. During the interview process, we saw a lot of amazing, amazing candidates, and Chloe consistently came back with the clearest vision, and the most original ideas and understanding of what a Vogue in-- Well, I don't think we can talk in 5, 10 years anymore, in two years is going to look like.

David Remnick: What are the specifics?

Anna Wintour: She understands a newsroom. She understands mediacy. She understands culture. She understands completely that fashion doesn't exist in a vacuum, that it's a result of many different forces, whether it's something that might be happening in music, or film, or politically, and wants to put it into that kind of a context. Plus, she has a great sense of humor.

I mean, her story that she thought of this summer called Doge. I mean, it went through the roof with our numbers, and it was so much fun just to look at all those crazy dogs dressed up with earrings and beautiful collars, and celebrities from all over the world were sending their dogs, so she has a really good balance about what works.

David Remnick: Now, why step aside from American Vogue now? Have you been thinking about this for a long time?

Anna Wintour: I have been thinking about it for some time. It felt like this was the right time, because we're seeing so much change in fashion when we go off to the shows. Well, actually, I think they start next week. I believe there's well over 14 new creative directors in very high level positions all over Europe and some here, so it seemed like a good moment to bring in someone with a different perspective, and a different generation who could look at things in a new way.

David Remnick: Now, at first, in 1988, you burst on the scene as the new Vogue editor by putting somebody on the cover with a pair of jeans on. In fact, I noticed that Chloe was wearing jeans.

Anna Wintour: Yes, she was.

David Remnick: In her photograph on the Vogue website. She may be signaling something.

Anna Wintour: I think that picture was taken a while ago, but she looked great, and similarly to Chloe, I had been working at Vogue as creative director before I took the position as at American Vogue and also at British Vogue, so I also had some history. I think that's a very helpful way to start a new job, to understand how things work, who the people are, how decisions are made, and maybe you want to do things in a different way, but just having that is a huge advantage.

David Remnick: You have this odd situation now. You are not leaving your office, your physical office. You've got two huge jobs at Condé Nast, where you're the editorial of-- Well, of everything. You've got a lot going on, whether it's the Met Gala, or your other interests, and family, and all this, but you're right there, and your successor is down the hall, and Chloe said this to The Times today, "The truth is that no one's going to replace Anna," and so you're going to be right down the hall, and The Times wrote that both women have acknowledged the strangeness of this arrangement. How will this work?

Anna Wintour: Well, I think I implicitly trust Chloe, and I want her to succeed to the best possible degree. I think that she is beloved by her team. I think that she will require from all of us, not just me, from everybody, and from our editors group, from everybody here at Condé Nast, I think she'll-- She's the kind of editor that welcomes that. She doesn't work in any way in isolation. She's very open, she's very communicative. Her office is always full of people. She's very outgoing.

David Remnick: Will you be in her head, is what I mean? In other words, will she be trying to edit to-

Anna Wintour: I don't think so.

David Remnick: -please you, or to do--[crosstalk]

Anna Wintour: I absolutely don't think so. I think she's very much her own person. She has her own point of view. I mean--

David Remnick: How does it differ?

Anna Wintour: She's-- I think, she looks at things with a more, what's the right word? Not eccentric, quirky, unusual point of view. She comes at things from different angles. She's interested in fashion, but not obsessed with it, so that there are many levels that will weigh into her decisions. I think that she will not be drawn into, I don't like this word, but a "fashionista" conversation. I think that she will be able to step back, and look at things in a very healthy context. She's--[crosstalk]

David Remnick: Has the fashionista conversation dissipated, and disappeared in the contemporary world?

Anna Wintour: I think it exists very much in certain circles, and I think that what I love about Chloe is that she's an insider, but she's also an outsider.

David Remnick: What you're saying is, she doesn't want to be an Anna Mini Me?

Anna Wintour: No, not at all, and that was very clear during the interview process, and all the conversations that we've had. She wants to be her own person. I think she's not interested in those kind of comparisons. She just wants to be herself, and show herself, and prove herself, and make news, as I'm sure she will.

David Remnick: When you took over Vogue, Vogue had this immensely central place in this very big business, and in the fashion discussion, and now we live in an age of Instagram, TikTok, the technological democratization of fashion itself, and God knows what role AI is going to play, so how is her job different from yours?

Anna Wintour: Well, I look on Vogue as being the world's biggest fashion influencer. If you look at our reach from a social perspective, American Vogue alone has well over 50 million followers. If you look at the numbers that we receive on our site, or on our app, or the way whatever we may be putting across any of our platforms are received, or seen, or heard, that the influence is immeasurable, so I think in a way, Chloe has a much bigger platform than I had. When I came in, I always remember Alex Liberman telling me.

David Remnick: The editorial director in those days. A very famous figure.

Anna Wintour: Editorial director, wonderful figure. My mentor and my boss for many years. He used to tell me that they would go to Jones Beach in the afternoons, because there wasn't that much to do. Can you imagine that, David?

David Remnick: I really cannot.

Anna Wintour: I don't think that Chloe will be spending any of her time at Jones Beach in the afternoon, but I actually think, if I remember when I started at American Vogue, and it was solely a print publication with a few events, and genteel parties that we had to go to. Now, she has all these different ways of talking to our audiences, whether it's through social, or TikTok, or print, or events which are a huge part of what we think about today, or any of the many, many ways that we reach our audiences.

How amazing, how exciting, how interesting, how culturally relevant is it? It's so fascinating to see how much Vogue means to our world. I mean, I was flooded with emails this morning. It does mean a lot to people within the fashion world and without, and that's a great honor, and it's a great responsibility.

David Remnick: You mentioned print. When I started in 1998 at The New Yorker, I thought I was about to lose my job within a month. SI Newhouse, of course, owns the joint and ran Condé Nast completely, and thoroughly in those days, asked to have lunch with me at his apartment. Usually, we went to some restaurant.

Anna Wintour: Yes.

David Remnick: I thought, "Well, this is a world record. You've really done it." He took out--

Anna Wintour: [chuckles] Was it a yellow pad?

David Remnick: He took out a yellow pad, and we were losing money at that point. I won't say how much, but it was not insubstantial, and he said, "If we went from weekly to bi-weekly, we would save millions and millions of dollars, and we would suddenly become profitable." Then, he said something that I'll never forget. He said, "It's your decision." It was the editor's decision to make this very consequential.

I decided pretty quickly that that would signal, in fact, something terrible. Not only it would be terrible for The New Yorker, it would be terrible for businesses, is that it would signal the Life magazinization of The New Yorker. We live in a very different time now. The Internet was not in play then. What does print mean going forward for Vogue? Chloe, in fact, mentioned that she wants to have fewer print editions. Why?

Anna Wintour: Well, I think we all look at print as something that is collectible, and something you might want to archive and hold onto, and I think it also has to represent a news-breaking moment, like you need a reason to put somebody on the cover for any of the stories that you might be running inside. I think that's what Chloe was talking about, that it has to feel in a way, more important, more substantial and separate from the day-to-day news breaking stories that we put up on your site, or our site.

David Remnick: Yes. It's not purely a decision about decline of print advertising, or it's not a purely business decision.

Anna Wintour: I think it's the right decision, and I think there's a lot of different factors that play into it, and obviously it's something that we all need to sit down, and talk about and figure out what the right path is going forward, but I think it comes from the idea that print has to feel more substantial, and more important. I mean, it's our runway show. If you think about how many people actually go to a Vuitton fashion show, it's between 400 and 800 people, but then it goes out to millions and millions, and I think-

David Remnick: Instantly by Instagram, and, yes.

Anna Wintour: -instantly on live stream, whatever it may be, and I think print has that same responsibility. You're giving a message, you're making news, you're giving your vision, but it doesn't necessarily have to be over and over again many, many times a year. I mean, I think most of the big designers, probably, have six or seven shows a year, which is already a lot.

David Remnick: You're a very politically engaged person, and a very politically aware person, and it's no news to you that the world right now is in so many ways in really bad condition. How do you make a case that fashion is important in the midst of all that?

Anna Wintour: Well, I think fashion is always important. It's a question of self-expression, and a statement about yourself, and whether it's a loud logo you might choose to put on yourself, or something with a color, so I think fashion can say so many different things, and forgive me, David, but how boring would it be if everybody was just wearing a dark suit and a white shirt all the time?

David Remnick: Right.

Anna Wintour: I think people are individuals, and they ought to be able to express themselves, and it's a form of creativity, and that's why we need fashion, and we need great designers.

David Remnick: For decades, you've been known as the editor with exacting control over every spread, every-- Is that true?

Anna Wintour: Well, that's very much exaggerated?

David Remnick: Is it?

Anna Wintour: Yes. [laughs]

David Remnick: I don't buy that, that you don't say, "Yes", or, "No", on everything that's in Vogue?

Anna Wintour: Up to a point. I mean I oversee so many different Vogues now, that it's impossible to have that kind of detail. I think it's really important to surround yourself with people whom you admire, and that you respect. I really rely on the editors that we have there to, I can say, "I don't think this looks so great," but they can come right back and say, "This is what will work in this culture."

David Remnick: What I mean is, how deeply do you get into other Vogue's other magazines, either here in the United States, or around the world?

Anna Wintour: Yes. I mean, I-

David Remnick: How granular?

Anna Wintour: -in terms of Vogue, I look at every print issue before it goes to what's hypothetically called the press.

David Remnick: Thank God. [chuckles]

Anna Wintour: I will look at their sites. I can't understand all the languages. I look at all their social media, but it's-- I will make suggestions, and call and say, "Are we sure about this?" Or, "Why aren't we doing that?" There's no way that you can keep up with every single platform across all the territories, but I certainly keep my eyes out.

David Remnick: Did you ever feel like along the way, did you have a time, or a year, or a moment, you think, "Enough with this. I can do a lot of things. I just-- Enough."?

Anna Wintour: Actually, no, David-

David Remnick: Really?

Anna Wintour: -because I love what I do, and I grew up as you know, in a family of journalists, where we were always being dragged home from vacation holidays, as we would say in the UK, because some news was happening, and in those days you couldn't do email or Zooms, you had to be there. My dad was someone who always had to be there. He had to be in the newsroom, and that was actually exciting in a way, and our house was full of journalists, and politicians, and interesting people. I find that today just as exciting, and just as interesting, and I'm always more interested in looking forward than looking back. I do think sometimes we spend too much time on nostalgia.

David Remnick: How do you mean?

Anna Wintour: I think people always ask, "What was that based on?" Or, "What was your inspiration?" Sure, people have inspirations, and they have unconscious thoughts in their heads. True creative design, I'm talking about the fashion world, true creative designers, and I'm sure it's same with your world. It's original, it comes from their mind, not from somebody else's mind. Maybe they had some influences, but the idea is theirs.

When I work with Andrew Bolton, who's the chief curator at the Metropolitan Museum, we work very closely together every year on the Met exhibitions, and it's so fascinating and exciting, and interesting to see how his mind works, and how the ideas form, and yes, he reads a lot, he looks at a lot, but in the end, the original thinking is entirely Andrew's, so to me, that's a great artist.

David Remnick: I wonder how you felt when Alexandria Ocasio Cortez arrived at the Met Ball in a white dress slathered with the slogan "Tax the Rich."?

Anna Wintour: Yes, well, I'll tell you a story about that, David. She was actually sitting at my table, and I stand in the receiving line, and I don't see the people arriving on the carpet. I don't have a secret livestream coming, being zoomed into my earphone. I'm just standing there shaking everybody's hands, saying, "Thank you for coming," blah, blah, blah, so I said, "Thank you for coming," and she went by.

Then, I went up to her before we all sat down at the table, I said, "I just love your dress." Because I'd only seen her-

David Remnick: The front.

Anna Wintour: -from the front, and it wasn't until the next day that I understood what had happened, so, fortunately, I had a wonderful evening.

David Remnick: [laughs] When you saw it later, how did you feel?

Anna Wintour: Well, it's something going back to what we were talking about before. I think everybody uses fashion in different ways, and obviously, that was something that was important to her.

[music]

David Remnick: This is The New Yorker Radio Hour, and I'm speaking today with Anna Wintour. We'll continue in just a moment.

[music]

This is The New Yorker Radio Hour. I'm David Remnick, and I've been speaking today with Anna Wintour, who's stepping back from editing the US edition of Vogue after nearly 40 years. Chloe Malle will be the new head of editorial content there. Years ago, when I was new at the job of editing a magazine, I asked one of Anna Wintour's deputies why she commanded such respect.

The answer was this, it's because she knows what she wants. Over time, I learned what that meant. It wasn't that she knew everything, or knew better than everybody, but she had a clear sense of what she wanted her publication to be about. She had a determination, particularly now, when the media business is unpredictable, to put it mildly, how to figure out the future. To make things work, to make mistakes, and yet try again.

Wintour comes from a distinguished journalism family. Her brother is an editor and reporter, and her father was editor of a London newspaper. He helped steer Anna into a career in fashion, and she began working as a teenager. Your father was at the London Evening Standard.

Anna Wintour: Yes.

David Remnick: Your brother is-- Is he back from Iran?

Anna Wintour: [chuckles] He just came back, yes. Safely, thank you.

David Remnick: Thank you. Is at The Guardian.

Anna Wintour: Yes.

David Remnick: Journalism is in your blood, and you found your place in it, God knows. The most interesting part of any biography for me is not the later big triumphs, as interesting as they can be, but how somebody becomes themselves, in a sense, how they invent themselves. When you think about that, how you became the Anna Wintour that at least the public knows and understands. Where do you think that all came from?

Anna Wintour: I think I was so lucky, as we were discussing before in my upbringing, and meeting all these people, and knowing that I wanted to work in journalism, in media, but being very aware of my father's success in Fleet Street, as it was then called in Fleet street, and not wanting to be part of his world, and trying to make my own mark, and filling out all those stupid school forms that you have to do, and asking my dad, "Well, what shall I fill in when you write what you want to be?" This is a true story. He said, "Well, you just write you want to be editor of Vogue." Yes.

David Remnick: No. Age what?

Anna Wintour: I don't know, 13, so I wrote that in, and then I felt confident, and, yes, this was something that I could work towards. The other thing working, my first job was working in London. There's no money, there's no staff, there's no teams. You have to learn how to do everything.

David Remnick: What was the job?

Anna Wintour: My first job, I worked at Harper's Queen and I was in the fashion department, and you had to cover the market, go on shoots, write the captions, lay it out, go to events, go to the shows. It was just the original multitasker, and I think that--

David Remnick: You have to know how to operate a needle and thread.

Anna Wintour: [laughs]

David Remnick: Sewing.

Anna Wintour: Yes. I was never any good at that. Never any good at that. [crosstalk]

David Remnick: [crosstalk] for you?

Anna Wintour: Yes, awful. When I came to the States, and there was a shoe editor, and an underwear editor, and a fabric editor, it was also siloed. I felt very confident because I knew how to do everything, and that that was the best training.

David Remnick: Wait, you determined your final-- Not final destination, as it turns out.

Anna Wintour: It was helpful.

David Remnick: At that early age, I'm going to be the editor of Vogue, which is a little bit like saying, "I'm going to play shortstop for the Yankees," and that was Derek Jeter at 19.

Anna Wintour: Well, it was a goal. It wasn't-- It was a goal to work towards, and obviously, there were many ups and downs along the way, including getting fired from Harper's Bazaar, because I was told I would never understand the American market.

David Remnick: Tell me about the firing.

Anna Wintour: [chuckles] It was very brief. It was very brief.

David Remnick: The conversation?

Anna Wintour: Very, very brief. [chuckles]

David Remnick: What was the start? We've all done it. How do you do it?

Anna Wintour: I think back, how do I try and be kind, and thoughtful, and listen to what people have to say? I was not given that. I was basically told to leave, but I think everyone should be fired once. You've probably never been fired, David, but--

David Remnick: I've only had two jobs, so far, so good.

[laughter]

Anna Wintour: It helps you get everything into proportion, and pick myself up, and eventually landed at New York Magazine, where my multitasking really came into full use, because there wasn't anyone there that understood anything that I was doing, and I was very lucky to work for Ed Kosner, who was a wonderful editor, and gave me free rein, and that's where I caught Alexander Liberman, the editorial director of Condé Nast. Then, I moved over to American Vogue.

David Remnick: I hope this is not a sexist question, but maybe we could ask it of men, too, I hope we do. How did you develop your look, and why?

Anna Wintour: Well, for my hair, it was always pretty much this way, and then some--

David Remnick: It's not a Louise Brooks influenced anything?

Anna Wintour: No, some British hairdresser decided they were going to experiment on me, and they cut it into three layers, and it was honestly the worst haircut you've ever seen in your entire life, so I think I wore a hat for a year, and then after that I resolved not to cut my hair, except this way ever again. I mean, the glass is just because I'm very short sighted, but they also help me get through situations.

David Remnick: Were you bored to death?

Anna Wintour: You said that, not me.

David Remnick: I did. [laughs] I think I'm going to take it up. Another thing that you're known for is your ability to do about 3,000 things in a given day. Give me how your days typically go. When do you get up? What do you do? And how is it carried out?

Anna Wintour: Well, I get up really early, 4:30, five o'clock, and I read online the papers, all the English papers, and The Times. Then, I have a lovely walk through Washington Square park, where you see a very interesting slice of life, and go to the gym, and then I run back, and then--

David Remnick: You were a runner when you were a kid, right?

Anna Wintour: Yes, I was.

David Remnick: A good one.

Anna Wintour: Yes. My grandfather was a very, very fast runner. He ran for Harvard, and I was always being encouraged to run, to go into serious training, but I just-- I didn't take that path. It was the '60s in London, so I took another path.

David Remnick: [laughs] You took the other path.

Anna Wintour: I took another path, many other paths. Then, I go to the office, and then the day starts.

David Remnick: Then, the day starts?

Anna Wintour: Yes.

David Remnick: You've said you'd never write a book about your life. Why is that?

Anna Wintour: Never. I don't think I'm that interesting, and--

David Remnick: Okay, that's where you're wrong.

Anna Wintour: Thank you, David, but I really-- I don't. I just-- It's not a story I want to tell.

David Remnick: Because it's too personal, it digs too deep, or actually you're bored with it? You're bored with the past?

Anna Wintour: The past is done, and I can't rewrite it. Of course, there are lots of wonderful things about it too, but it's just not something that is of any remote interest to me. Are you ever going to write the story of your life, David?

David Remnick: I don't think so.

Anna Wintour: There you go.

David Remnick: I'd like to learn something new, like Chinese or something. There was a time that even unschooled people like me knew about, or a little bit about designers of huge influence, at least, knew their names, or sketch of what they did. Lagerfeld, Miuccia Prada, who's still very much around. Galliano, Marc Jacobs, still a bunch around. Suddenly, nearly all the fashion houses are led by young, or younger designers whose names are not particularly well known.

Anna Wintour: They will be, and many of them are.

David Remnick: Not many are women either.

Anna Wintour: No, that's--

David Remnick: How do you assess this new scene that--

Anna Wintour: Well, it's one moves, and then it's like a pack of cards.

David Remnick: Why?

Anna Wintour: Well, because one designer goes from A to B, and then that leaves an opening, and then somebody else is slotted in, and then there's another opening, but it is totally true that this is the first time that I can ever remember where we had so many openings in so many high profile houses, but it's also incredibly-- I think it will be a very creative moment, because if you talk to these designers, of course, they're very aware that they're all making their debuts in the next few weeks, so all eyes, not just on them, but on all of them, and I think they will all make each other better.

David Remnick: Who are you most keenly watching?

Anna Wintour: All of them. I mean, I think they all bring different points of view, some degrees of experience, some brand new. Some less known, some known, but what I think is great about all of them, is that they are very original thinkers, and I think that they will not be defined. They will respect, but they will not be-- Like Chloe. They will respect, but not be defined by their past.

I think Jonathan Anderson at Dior is going to be-- Have an incredible show, an incredible run at Dior. I'm very excited to see Mathieu Blasy at Chanel. He was at Bottega before, and Jack and Lazaro, who are Americans going to Loewe. I mean, those are just three. I mean, Sarah Burton, a woman at Givenchy, she worked for McQueen for so many years. Louise Trotter at Bottega. I mean, it's just a long, long list. Then, there's the designers like Demna, that was at Balenciaga, has now gone to Gucci, and Pierpaolo, who was a Valentino, has now gone to Balenciaga, so it's-

David Remnick: The cards have been shuffled.

Anna Wintour: -snakes and ladders everywhere.

David Remnick: My colleague Rebecca Mead recently profiled Jonathan Anderson, who's now, as you say, at Dior, and he told Rebecca that he prefers to think of fashion houses not as luxury bastions, but as cultural brands. He says, "Luxury is elitist," and he wants to keep luxury at arm's length, he told her. How do you view luxury at this point? Is it something that you embrace? Is it something that--

Anna Wintour: Well, I hate that word, don't you? [chuckles]

David Remnick: Well, it rarely enters my thinking, [chuckles] but go ahead.

Anna Wintour: It doesn't mean anything. It seems like a dated--

David Remnick: It sounds to my ear like expensive.

Anna Wintour: Yes, and it feels dated to me, and something that-- I think I like the idea of creativity, and what does that mean, and how you bring in a community in all kinds of different levels, whether it's couture, or runway, or a pair of sneakers, you're investing in somebody's creativity and vision, and to me, that's much more interesting than the idea of luxury. I mean, I don't really even know what that word means. It's so overused. I think it's lost its heart.

David Remnick: In some ways, it might be an illusion, but the economy is riding pretty high, and yet a lot of fashion houses are very anxious about the economy.

Anna Wintour: Well, there's many reasons for that. I mean, I think, first of all, there's been so much change, that I think a lot of the normal customers are waiting, because they want to wait and see what the new designers are going to bring. They don't want to seem like they're behind, or they're not in step with whatever direction a designer might be going, or they were someone who liked what the old designer did, and they're not sure yet about the new one, so there are lots of different reasons, but I also think that the industry has been very hard hit by the tariffs, and all this.

David Remnick: Trump's tariffs are going to affect things?

Anna Wintour: They already-

David Remnick: They already have?

Anna Wintour: -have because people would move their businesses out of China, and into India, and then you saw what happened in India, so it's hard to be able to plan long term, and also, the fashion industry already has 12.5% tariffs on a lot of what they produce, so to stack it again is going to make it even more difficult, particularly for the smaller businesses.

David Remnick: You have made Vogue a political magazine in many ways over the years. You yourself are a political person. You've been involved in fundraising, and more for Hillary Clinton, and for the Democratic Party in general. Tell me about that decision.

Anna Wintour: I think my personal values are very important to me, and I also have tried to be balanced in our coverage. I also believe that, what I believe, many of our audiences do as well, so it's a tough time for Democrats. There's no question, and hopefully, somebody will emerge in the not too distant future that will challenge our current administration.

David Remnick: Do you see anything of that?

Anna Wintour: Well, I've been impressed by Governor Newsom. I think he's certainly making a stand, and obviously, I'm sure there'll be many other candidates that will emerge hopefully soon.

David Remnick: Hopefully soon. [laughs] It seems pretty grim at the moment, though.

Anna Wintour: Well, we have time.

David Remnick: There was a movie that you may have heard of called the Devil Wears Prada. At first, and we didn't know each other very well when that came out, Condé Nast had a kind of different alignment than it does now, and I should say it's changed, largely, because of you, and having editors' meetings, and the editors got to know each other a lot better than they used to, which is a gift. When that first came out, were you hurt by it? Then, you seemed to embrace it in a certain way.

Anna Wintour: Well, I went to the premiere wearing Prada, completely having no idea what the film was going to be about. I think that the fashion industry were very, very sweetly concerned for me about the film, that it was going to paint me in some kind of difficult light.

David Remnick: Cartoonish.

Anna Wintour: Yes. A caricature. First of all, it was Meryl Streep, which, fantastic. Then, I went to see the film, and I found it highly enjoyable, and very funny. Miuccia and I talk about it a lot. [chuckles]

David Remnick: Miuccia Prada. Yes.

Anna Wintour: I say to her, "Well, it was really good for you," and you can imagine what she says back, but in the end--[crosstalk]

David Remnick: No, I can't. What did she say back? [chuckles]

Anna Wintour: [laughs] No, I think, listen, it had a lot of humor to it. It had a lot of wit. It had Meryl Streep. I mean, it was Emily Blunt. I mean, they were all amazing, and in the end, I thought it was a fair shot.

David Remnick: At a certain point, celebrities came to the cover of Vogue. Was that something you did with hesitation? You did it pretty early on. I think Madonna might have been one of the first.

Anna Wintour: One of the first. Yes. I felt that times were changing, that time was different, and that our audiences, our readers, were looking at fashion, not just through the lens of a model, as was primarily on the cover before that. Although, of course, if you think back to the days of Mrs. Vreeland and others that they did, they had people like Candice Bergen, Chloe's mother or--

David Remnick: who played the editor of Vogue on Sex and the City. [chuckles]

Anna Wintour: Yes, or Mia Farrow. I mean, it wasn't unheard of, but I think that we recognized a change, we saw a change. Madonna, of all the many celebrities that we've had on the cover of Vogue, she certainly loved and epitomized fashion, and was fearless with it, and had fun with it. It just felt like the right time. I remember being on this plane, and sitting next to a straight-laced, straight, wearing a suit gentleman, and he asked me what I did, and I was telling him, and he said, "Well, Vogue means to me, Audrey Hepburn, Katharine Hepburn, never Madonna," and that made me think, time to change. [chuckles]

David Remnick: [chuckles] What are you most proud of having published at Vogue?

Anna Wintour: I couldn't possibly choose one piece, or one story, or one cover, David. I think it was very-- It was quite moving being in the meeting this morning, talking to all my colleagues about how I felt about Chloe, and what a great job that she was doing. I think the thing I'm the most proud of, is bringing in over so many years, different talent, writers, photographers, videographers, editors to Vogue. I mean, that to me, and I'm sure you feel to some degree the same way. It's about who you surround yourself with-

David Remnick: Entirely.

Anna Wintour: -and in the end, that's by far the most important accomplishment to me.

David Remnick: Were you emotional at this meeting?

Anna Wintour: Well, I've been thinking about it for such a long time, [chuckles] but, no, I was actually thrilled and excited, and happy for Chloe, and excited for myself to look at things in a different way.

David Remnick: Does it mean that you'll have more free time? I can't imagine Anna Wintour with free time.

Anna Wintour: Well, I think I'll have--

David Remnick: Only two jobs now.

Anna Wintour: [chuckles] Yes, two jobs. [crosstalk] I am remaining fully committed as theater and tennis advisor to Vogue. That's going to be my next big chapter.

David Remnick: Okay, I'm holding you to that. Now, I think we're now ready for what we call the Lightning Round. Are you ready?

Anna Wintour: Yes, of course.

David Remnick: Okay. Who is the greatest fashion designer of your era as editor?

Anna Wintour: David, I only look towards the future.

David Remnick: [chuckles] What was the most triumphant or influential fashion show of that era?

Anna Wintour: Ditto.

David Remnick: Most lamentable fashion trend of your era?

Anna Wintour: DayGlo.

David Remnick: Okay, true or false? Jeff Bezos was interested in buying Condé Nast.

Anna Wintour: Well, actually, I heard that he called you about that.

David Remnick: False. Good turn. [chuckles] You are actually-- This is true or false, you are actually thrilled when assistants move at a glacial pace.

Anna Wintour: Nobody at Vogue moves at a glacial pace. Least of all my assistants.

David Remnick: This is the most important question of all, Anna. Finally, I wore a decent shirt, and an actual jacket today in deference to you and the occasion, but still, I think it's fair to say that I'm not known for my impeccable sense of style. Anna, is it hopeless? Where can I possibly begin?

Anna Wintour: [chuckles] David, I'm very touched that you wore a jacket, but I really like you in The New Yorker sweatshirts. [chuckles]

David Remnick: [laughs] There I was, living up to the sartorial standards of the Late SI Newhouse.

Anna Wintour: [chuckles] Thank you for having me.

David Remnick: Anna, thank you. [music]

Anna Wintour has been Editor of Vogue since 1988. She'll remain the chief content officer for Condé Nast, which also publishes The New Yorker, and if you missed any of our conversation, you can find the video on The New Yorker's YouTube page.

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