Nothing excites Anna Wintour like the annual unveiling of Vogue’s September issue—well, maybe Wimbledon finals or opening night of a new Broadway show, but the September issue is high on the list.
Wintour recently met with me and Chioma in her office’s sitting area to discuss the most exciting moments in the biggest issue of the year, her first fashion memories, how her father’s work ethic inspired her, and what she likes to do in her downtime.
The September cover, styled by Edward Enninful and photographed by Rafael Pavarotti, was particularly momentous for Wintour, who fondly recalled a similar cover from the 1990s featuring the same quartet of legendary supermodels—Christy, Naomi, Linda and Cindy—but photographed by Peter Lindbergh in the supers’ heyday. She also remembered her first September issue as editor-in-chief of American Vogue, featuring Naomi Campbell, and noted that between the four of them the supers have graced more than 40 American Vogue covers.
Wintour goes on to mention some of her personal favorite moments in the issue, all of which, like the cover, return to subjects Vogue has covered before: from the profile of Josh O’Connor timed to his latest film, Challengers (its release date has been delayed due to the Hollywood strikes); to the article on Zadie Smith and her new historical novel; to Gabriella Karefa-Johnson’s glamorous punk editorial photographed in Japan with model Devon Aoki, and evoking the late, great high priestess of punk, Vivienne Westwood.
When we spoke, Wintour was about to head off to Long Island for some well-earned vacation, where you can find her in her garden, playing tennis, and spending time with her grandchildren and extended family. You’ll just have to listen to find out what her grandchildren call her.
Chioma Nnadi: This is The Run-Through. I'm Chioma Nnadi.
Chloe Malle: And I'm Chloe Malle. And it is that time of year.
Chioma Nnadi: Oh, yes it is. The most important and exciting time of year around here.
Chloe Malle: I feel like it's like a Christmas carol.
Chioma Nnadi: I know [laughs].
Chloe Malle: It's the most wonderful time...
Chioma Nnadi: It's the most wonderful time...
Chloe Malle: [laughs]
Chioma Nnadi: I mean, it's a September issue, guys, if you didn't already know. [laughs]
Chloe Malle: So we wanted to talk to you, the woman who has made so many iconic September issues... The Wizard of Oz of September issues, our boss, Anna Wintour.
We sat down in her office at Vogue’s headquarters, in the World Trade Center, and we wanted to chat with Anna about everything from her earliest fashion memories, to how her father influenced her work ethic, and [laughs], uh, what her grandkids call her... Which I was surprised and delighted by, and of course about the making of this year's incredible September issue.
Chioma Nnadi: But of course, we started off by asking her about why the September issue is so important, about the making of this year's September issue... Which of course, had all the supers on it. All your faves. Linda, Christy, Naomi, and Cindy.
Chloe Malle: No last names needed.
Chioma Nnadi: No. None.
Chloe Malle: No last name needed for Anna either.
Chioma Nnadi: No.
Chloe Malle: Not on this podcast, anyway.
Chioma Nnadi: No, no.
Anna Wintour: So well, obviously the cover is always the most exciting thing for any issue, but particularly for the September issue. And working very, very closely with our colleagues, and particularly, uh, at British Vogue... And particularly Edward Enninful, who is global editorial director of Vogue in Europe, and editor-in-chief at British Vogue.
We were very, very intrigued to hear about the Apple documentary, starring four of our favorite supermodels. What we have on the coverline is “The Greatest of All Time: Linda, Christy, Naomi, and Cindy.” And so, those are the four great models on the cover, photographed by young talent, Rafael Pavarotti. And between them, I believe just in American Vogue alone, they have over 42 or 43 covers.
Chloe Malle: Wow.
Anna Wintour: I think this would be their 43rd cover. I think, I think it's the first one where they've all appeared, uh, together, although they did do a similar cover way back in the '90s, uh, with Peter Lindbergh.
And I think we are all very, very intrigued by the interest in the '90s, both from designers and, and a, a documentary that we ourselves at Condé Nast are working on... Like, what the '90s meant to fashion. And I'm not sure if either of you saw the 1997 exhibition that was on in Paris?
Chioma Nnadi: I didn't—
Chloe Malle: No.
Chioma Nnadi: I wasn't able to catch it while it was on, but I heard it, that-
Anna Wintour: Yes.
Chioma Nnadi: ... it was incredible.
Anna Wintour: It was really reinforced, I think, seeing it. Uh, that that was such a pivotal moment in fashion. It was a, an exhibition about 1997, where, you know, so many designers were discovered. It was when Nicolas Ghesquière went to Balenciaga. It was, uh, you know, also the scene of a great tragedy. We lost not only Princess Diana, we lost, uh, Gianni Versace.
And I think if we look back at the '90s, it was... I think it was when models really captured the public i- imagination in a way that was unlike anything we had seen before. So it felt right, since the Apple were doing this marvelous documentary, that we would pay tribute to them, because they've been so much a part of our history for so long.
We also thought it might be timely to revisit a couple of celebrities, uh, artists, that we had featured in the magazine before.
Chloe Malle: Who are some examples of that?
Anna Wintour: Well, one is the, uh, young actor, Josh O'Connor, whom we all I think came to... Came to our attention first with the film God's Own Country, which was the Yorkshire equivalent of Brokeback Mountain.
Chloe Malle: [laughing]
Chioma Nnadi: [laughing]
Anna Wintour: Um, uh, where, in which Josh, I think, was truly extraordinary, and I think it's where he caught the attention of people like Stephen Daldry.
But, uh, he captured most people's, uh, attention when he played the young Prince Charles in The Crown. And he is appearing... We don't know when yet, in, in many movies, but the one that we were intrigued was, was Challengers... Of course for me, because it was a film about tennis, with Zendaya-
Chloe Malle: [laughs]
Anna Wintour: ... and the young actor, uh, Mike Faist. And he's remarkable in it. He even learned under the guidance of Brad Gilbert, to play tennis.
Chloe Malle: Wow.
Anna Wintour: And then Zadie Smith, who's been in, in, in, in the magazine and been, been with us over many, many times.
Chioma Nnadi: Why is the September issue such an important issue?
Anna Wintour: Well, I think it's a combination of, uh, our history that September's always been the most important month. I think it was amplified by the, the documentary that was made, uh, many years ago, The September Issue. I think there is an excitement around that time of the year. Uh, fall clothes. Uh, by nature, maybe more, more to look at, more to photograph, more to take videos of, more to talk about [laughs] on podcasts,-
Chioma Nnadi: [laughs]
Anna Wintour: ... uh, than, than the spring collections... Uh, as wonderful as they can be. I think there's just a sense of everything starting over.
When I think back to when I first started working at Vogue, and was thinking about my first September issue... Which actually had Naomi Campbell on the cover, I think I was a little bit naïve in understanding the importance of that issue. Because to me, Naomi was the model of the moment, and I had absolutely no hesitation at that time in putting her on the cover or choosing her to be our cover star.
But there was a sort of, um, peculiar ritual that you had to go through back then, when you would present, uh, the issue to the number of executives... All of whom were men. And they were quite surprised, and I think not a little, um, nervous about the idea of having Naomi on that cover, but to me, there was absolutely no doubt. So, it's a, a nice moment, to have her back on the September issue, in the company of, you know, great friends and collaborators... For her, and for us over many years.
And of course, September now is, is not just print... It's so many other things as, as you both know.
Chioma Nnadi: Vogue World.
Anna Wintour: Yes.
Chloe Malle: [laughs]
Anna Wintour: Video, and, and digital, and podcasts,-
Chloe Malle: Podcasts.
Chioma Nnadi: Yes.
Anna Wintour: ... and everything else that-
Chioma Nnadi: Yeah.
Anna Wintour: ... makes up, uh, content in Vogue today.
But of course, you're absolutely right, Chioma. We're super excited about our second Vogue World, which is gonna take place in, in, in the UK. And, um, I think after the success of Vogue World here in New York, we wanted to live up to its name, and start to take it around the world.
And we were very anxious to support the performing arts in the UK, because they have had such devastating government cuts. That will take place in a theater, and it will be a tribute to theater, musicals, opera, dance, and everything else in-between. And of course, fashion, under the, under the guidance and directorship of the great Stephen Daldry.
Chioma Nnadi: And the net proceeds go to...
Anna Wintour: Yes. All the ticket sales and also, um, many very, very generous donations that have also been given to us, would... They will all go to support different arts communities.
Chioma Nnadi: That's super exciting.
Chloe Malle: Anna, what's your first fashion memory?
Anna Wintour: Well, I grew up in London at a time where, you know, fashion was breaking out in a way that it hadn't before, and it became much more democratic and fun. It was, you know, the late '60s, early '70s. And I think the-
Chloe Malle: What were you wearing? Were you wearing mini dresses?
Anna Wintour: I'm sure I was.
Chloe Malle: [laughing]
Chioma Nnadi: [laughing]
Anna Wintour: But I think that it was a breaking down of class barriers, and, and, and people mixing much more... Not just being sort of boxed into... In a cer- into a certain way of life, which I think was certainly the, the case in, in the '50s and, and, and a little bit in the '60s.
I think it was a time of, of great freedom and of breaking down of barriers. So that obviously was amplified by what people we wearing, and also the music, and film, and, and culture all coming together. So, it was a super exciting time. I'm not sure that I have a first f- fashion memory, but I certainly have a memory of everything being much more open.
I mean, when I was, you know, a very young girl, I, I l- I lived in a situation where you got dressed for dinner, and women would leave the table-
Chloe Malle: Wow.
Anna Wintour: ... after the main meal-... So the fact that that was all being thrown out the window, was, you know, obviously a great relief to me.
Chloe Malle: [laughs]
Anna Wintour: And I'm sure, to many.
Chloe Malle: Ah.
Chioma Nnadi: You've been to so many fashion shows. Can you remember the first fashion show that had you on the edge of your seat, goosebumps-style?
Anna Wintour: S- fashion shows that... I l- I like going to the movies. It's always about... While reading a book, it's about who's telling you the best story.
Chioma Nnadi: Right.
Anna Wintour: And I think... It's so interesting to me, how the designers in London who managed to make incredible shows with no money... And just the way they produced content for so many years with, with, with no money, they seem a- able to do it in a way i-... They could go bankrupt the next... The, the next week, but they somehow managed to tell stories and to create an atmosphere and electricity around the work that they're doing. In a way that is also, as we were talking about the, the '60s and the '70s, very free. And maybe they don't have the weight of a corporation or a, a PNL sort of weighing so heavily on their shoulders, that they have that sense of freedom and exuberance that is always quite, quite remarkable.
So I wouldn't want to pick one, Chioma. There have been so many. But I do always think that the English designers have a sense of story-telling. I think about the great... Late, great Alexander McQueen, or John Galliano, or, you know, some of the younger designers working in, in London today. The, they, they, they tell a story in a way that I think is, is very enchanting.
Chioma Nnadi: Mm, agreed.
Chloe Malle: What are you excited about fashion-wise for fall? What is the mood of fashion right now? Are there any... Have you purchased any clothes yourself that you're excited to wear?
Anna Wintour: Um, I'm not that organized.
Chloe Malle: [laughing]
Chioma Nnadi: [laughing]
Anna Wintour: I haven't got that far. Um, I'm thinking... [laughs] I mean, I'm trying to figure out what I'm gonna wear to Vogue World. But, um,-
Chioma Nnadi: [laughing]
Chloe Malle: [laughing]
Anna Wintour: ... I was thinking maybe something gold. I like the fact that it's quite dressed, and it's quite ni- '90s, the way that, uh, Edward showed in that brilliant portfolio that he did with all the, the four girls. I love the evening story, that we shot at the Perelman Center.
We also have an homage, we're back to British designers again. But Gab went to Japan for a wonderful story that was what we were calling “Glamorous Punk.” But really I think in all of our minds, we were thinking about the great Vivienne Westwood, who sadly left us this, this past year. And it was a really a tribute to her style, and her activism, and a sense of breaking down barriers... That we were talking about before, and her belief in her causes, and her extraordinary energy and belief in everything that she did. And I think that tribute in the streets of Tokyo, is, is, is such a fun Vogue story-telling moment.
Chloe Malle: The Run-Through will be back in just a moment.
Anna, I am curious what your m- schedule is like? You're so legendarily a workhorse, and what is, what is Monday morning [laughs]?
Anna Wintour: Well, I'm just an early morning person, Chloe, and I'm not someone that stays up late and goes to the after parties [laughs].
Chloe Malle: [laughing]
Chioma Nnadi: [laughing]
Anna Wintour: So I do think it, it's a very helpful time for me to figure out the day, the week, the month. I look online at all the British newspapers. I read The New York Times. I read The Wall Street Journal. If there's any-
Chloe Malle: All online? No print?
Anna Wintour: No print.
Chloe Malle: Oh.
Anna Wintour: And if there's any, any calls that I need to make to, to any of our global colleagues, that's a great c- calm moment to do that. I go to the gym. I walk through Washington Square Park, which is always an interesting experience.
Chloe Malle: [laughs]
Chioma Nnadi: [laughing]
Anna Wintour: And I, I try and be here, i- be in the office by 8:00, ei- 8:15, to, to start my day.
Chioma Nnadi: So, you... What time do you actually wake up? [laughing]
Chloe Malle: [laughing]
Anna Wintour: A quarter to 5:00.
Chloe Malle: Wow.
Anna Wintour: Yeah.
Chloe Malle: [laughs]
Chioma Nnadi: That's impressive.
Chloe Malle: Anna, I'm curious. I always have been amazed at your attention to detail, and especially now, as your role has gotten more and more global.
Anna Wintour: Mm-hmm.
Chloe Malle: I still find that you will read every caption in the magazine.
Anna Wintour: Mm. Mm-hmm.
Chloe Malle: Ho- how... Is there a lesson to be learned from that? Is there... Do you ever feel like you w- wish you were le- less focused on the details, because it's overwhelming? Or is...
Anna Wintour: I think growing up with a father that worked in news, and seeing his excitement and his energy around breaking news and breaking stories, I think that fed into me a great love of journalism... And following a story and creating a story, that I feel very lucky to have had and to have experienced, you know, throughout my life, really. It's, it's not a world that I've ever not had in my life. And I think that's what drives you, what channels caring and passion, and hopefully that, um, that is, influences the people that you're working with.
Chloe Malle: I was listening to an interview... You talking about your father, on, on the way here this morning, and I was wondering... If you had to describe to your father today... Or he saw how different media is,-
Anna Wintour: Mm.
Chloe Malle: What do you think he would be most surprised by, or what would be the biggest change from 50 years ago or 60 years ago?
Anna Wintour: Well, you know, obviously his life was... And his career, was very much around print newspapers.
Chloe Malle: Sure.
Anna Wintour: But you have to remember, Chloe, when he was working, there were as much as eight to nine editions a day.
Chloe Malle: Oh my gosh.
Chioma Nnadi: Wow.
Anna Wintour: Yeah, so-
Chioma Nnadi: Eight to nine.
Anna Wintour: ... it was just a nons- nonstop print, print, print-
Chloe Malle: Wow.
Anna Wintour: ... of these different... The racing edition, the morning edition, you know, the midnight ed-... You know, so it was just endless.
So I, I think the volume, it may have been more concentrated in one area, but it was just as big. And I think he would've been, as we all are, so excited by what media has become... And how you can reach so much... so, so much a bigger audience than you could when you were just a print publication.
So I, I think he would've been thrilled, excited, and ready to start the day probably at 4:00 in the morning. So.
Chloe Malle: [laughing]
Chioma Nnadi: [laughing]
Chloe Malle: You're a night owl compared to him.
Anna Wintour: I know.
Chioma Nnadi: [laughs]
Anna Wintour: No, he would leave very early. He would leave at 6:00 in the morning.
Chioma Nnadi: Wow.
Chloe Malle: Wow.
Okay.
Chioma Nnadi: Um, can you tell us what pre-release and final release meetings are, and why they're important and what happens in them?
Anna Wintour: Yeah, it's... It's when you release the, the, the print publication to the printers. It's sort of an archaic name, but we stay with a lot of archaic names. And it's, it's when we're... All the editors gather in a room, and, and look at the issues, and decide if the captions are wrong,-
Chioma Nnadi: [laughs]
Anna Wintour: ... or the headline is wrong, or there's something that needs a little bit more work... Or whether we want to take something in or out, or change a headline, whatever it may be. But it's an important moment, where we all come together and, and look at the work. And we do it twice, hopefully also to look for mistakes. Or, um, something like right now... We're in this situation where we're having to wrestle with that the SAG strike means-
Chloe Malle: Mm.
Anna Wintour: ... for all of us, and making sure there's disclaimers on pieces around any actors that we're promoting—they're completely within the guidelines at the time—a film…that [laughs] may or may not be coming out now, and making sure that we're protecting them as, as we... Well, we, as we should.
Chloe Malle: Anna, as you know, the podcast is called The Run-Through.
Anna Wintour: Yes.
Chloe Malle: And I was wondering if you cou-... I feel like people are very intrigued by what a run-through is.
Anna Wintour: Yes.
Chloe Malle: ... and I was wondering if you could just talk about that.
Anna Wintour: Well, I can tell you about my first experience with a Vogue run-through.
Chloe Malle: We would love that.
Anna Wintour: It was before I had-
Chloe Malle: [laughing]
Chioma Nnadi: [laughing]
Anna Wintour: ... the job that I'm in right now. And I was creative director of Vogue, and I was invited to a run-through in the editor... The then editor-in-chief's office, which was far larger than the office that we're sitting in now. And every single editor sat around the office in a small chair for six hours. The whole day.
Chioma Nnadi: Oh my God.
Chloe Malle: What?
Anna Wintour: And models would come in, um, and we would all look at them and make comments. And that was how a run-through was operated.
Chloe Malle: Wow.
Anna Wintour: So that was one thing, when I was lucky enough to be given the position that I'm in right now, that I thought I could speed up. [laughing]
Chloe Malle: [laughing]
Chioma Nnadi: So how, how long is the average run-through now?
Anna Wintour: Um, shorter than six hours [laughs].
Chloe Malle: [laughing]
Chioma Nnadi: [laughing]
So, we didn't really get into detail in the interview, but a run-through is basically a, a run-through of the clothing that goes into every single shoot editorial. So, so the stylist, and the sayings that... All the sayings that, uh... And we'll present all of these looks to Anna, and they'll decide which will be shot.
Chloe Malle: It's a very high-stress, high-stakes situation.
Chioma Nnadi: Yeah.
Chloe Malle: But, back to our interview.
Um, Anna, what's the best thing about getting older?
Anna Wintour: Well, I think it gives you patience. I, I think you learn that in the end, everything will be fine. And you just need to think about things calmly and rationally, and, and try and come out making the right decision. Um, and I guess there's not much left to surprise you.
Chioma Nnadi: [laughing]
Chloe Malle: [laughing]
Chioma Nnadi: You're very passionate about the philanthropic work that you do.
Anna Wintour: Yes.
Chloe Malle: Mm-hmm.
Chioma Nnadi: You fundraise for The Met. You also do a lot of work with God's Love We Deliver and the Youth Anxiety Center. Can you tell us about the Youth Anxiety Center, and how you got involved? And why it's an important issue for you?
Anna Wintour: Yeah. I mean, I think mental health among young people is something I became more and more aware of as my own children grew up. And realizing that there was just not enough support for young people at a very fragile moment of their lives, when they may look grownup and adult, but in fact, they, they're kids. So it was very i- important to me, personally and to many people close to me, that we do something about that.
And out of that, the Youth Anxiety Center was born, in connection with Columbia and Cornell. And to help young people who were suffering from depression, anxiety, and even unfortunately, suicidal tendencies. And this has been, I think, amplified by, by the pandemic. You know, it's really quite alarming to see how the numbers have spiked post- post-pandemic.
Chioma Nnadi: Mm.
Anna Wintour: But also, incredibly encouraging to see how much more open people are to t- be talking about it.
Chloe Malle: Anna, I was wondering if you would just tell us about your summer vacation? What, what are you going to do after the September issue comes out to sort of relax a bit?
Anna Wintour: Um, well, what am I gonna do? I, I have, um... I'm very lucky to have a garden that I love, and I spend a lot of time in, in the garden and I spend a lot of time playing tennis.
Chioma Nnadi: [laughs]
Chloe Malle: Nice. Fun. [laughing]
Um, and can we just ask you what your grandkids call you?
Anna Wintour: Dog. [laughs]
Chioma Nnadi: [laughs]
Chloe Malle: Really?
Anna Wintour: Yes. And I have a lot of dogs [laughs].
Chloe Malle: [laughing]
Chioma Nnadi: [laughing]
Anna Wintour: So, yeah.
Chloe Malle: They call you Dog?
Anna Wintour: Uh-huh.
Chloe Malle: Oh my gosh, how fabulous.
Chioma Nnadi: [laughs]
Anna Wintour: Thank you so much.
Chioma Nnadi: Yeah.
Chloe Malle: All right, thank you.
Chioma Nnadi: Thank you, Anna.
Chloe Malle: That's it for this episode of The Run-Through.
Chioma Nnadi: The Run-Through at Vogue is a production of Conde Nast Entertainment.
Chloe Malle: The show is produced by Suzie Lechtenberg, Chelsea Daniel, and Alex Jhamb Burns. It's engineered by Jake Lummus, Gabe Quiroga, and Kevin Bourassa, and mixed by Mike Kutchman.
Chioma Nnadi: See you soon.
Chloe Malle: Bye.