Fashion is a world where the “next new thing” is constantly celebrated, where designers must keep reinventing themselves or risk falling into obscurity.
Atop that world, Anna Wintour remains a strikingly durable and influential presence. Her image never changes: the midi-length, brightly colored print dresses; the immaculate bobbed hair; the chunky necklaces; and of course the dark sunglasses, which make it harder for everyone to know what she’s thinking.
In her new online MasterClass on leadership, the Vogue editor in chief is revealing at least some of what she’s thinking. (MasterClass starts at $30 a month to take as many classes as you’d like.)
She also describes her daily routine (she’s up by 5 a.m. and playing tennis before you’ve likely even smelled your morning coffee), opens a Vogue fashion meeting to the cameras (models were too young and thin in recent London shows, participants agree) and, in a segment sure to be catnip to many fashionistas, sits down with a Met Gala seating chart.
Wintour, who’s headed Vogue for more than three decades, also describes what she looks for in a job interview (she stresses that it’s not what you’re wearing), and in a meeting in her office (don’t “settle in” for a long chat, just saying).
Amid several weeks of nonstop fashion shows in New York and Europe, Wintour hopped on the phone from Paris this week to discuss the new online gig, her unabashed fandom for Broadway shows, her feelings about the latest trends on runways, and what advice she gives her 32-year-old daughter, Bee Shaffer (hint: it’s the other way around.)
This interview has been edited and condensed for length.
AP: You’re known as a fairly private, even mysterious person. What gave you the idea to do this MasterClass?
Wintour: Well, they came to me. But over the years I’ve been asked so many times by young designers and students for advice and counsel. So it seemed a great opportunity to use a MasterClass to really talk about my own career and particularly my experience with the CFDA Vogue Fashion Fund, where we’ve mentored so many young designers, just trying to be helpful to young people thinking about getting into journalism or fashion.
AP: It seems fashion is always about finding the next new thing. At least twice a year, designers have to come up with a new idea.
Wintour: Way more than that these days! You can go to a Fashion Week every week of the year. I just was on the phone being asked to go to Tokyo Fashion Week. It’s continuous today. It’s also an industry … in a state of reappraisal and structure. I think that’s why I’ve enjoyed it for so long, because it is always about change, and that’s very inspiring to me and very invigorating, whether it’s finding a new designer or understanding how we can talk to audiences in all these different ways.
AP: How have you yourself remained such a constant?
Wintour: I think it’s super important to understand your own vision. If you want to make a comparison, look at a great designer: It’s very interesting to me to see Maria Grazia (Chiuri) at Dior, how she has re-established the codes of that house … the way Karl Lagerfeld when he was alive always did at Chanel. He would recast it every season but there was always the jacket, always the bag, always the little black dress. He would just reimagine it and modernize it every season. (Also) I see sometimes when people become successful they stay within a comfort zone … within quite a small world. What I’ve always tried to do is challenge myself by looking at art, going to the theater, traveling, walking in the streets, seeing what people are wearing and always bringing in young people to contradict me, tell me about new things and question my choices.
AP: Speaking of theater, you’re a big fan. What show have you enjoyed lately?
Wintour: Well, the day of the Victoria Beckham show (in London) I went to see a musical, “Six,” based on the six wives of Henry VIII. And it’s completely Spice Girls meets the #MeToo movement. Everyone else in the audience was 16 years old. It was so much fun. Also “Betrayal,” in New York (with Tom Hiddleston).
AP: What else has struck you at recent shows?
Wintour: I do feel there’s a sense of optimism and joy coming through the strongest collections … The other thing I see happening which I think came across most strongly in in New York was that they’re very, very committed to diversity and inclusivity, and also re-examining what the fashion show is. They’re really looking at it as something that is very authentic and real and personal to each one of them. It’ not just girls walking down on a runway. It’s more about individuality and personality and who the designer is themselves. It seems that the fashion show itself is being rethought.
AP: At the Met Gala this year, we had a cheeseburger dress, a chandelier outfit, a strip tease on the carpet ….
Wintour: (Laughs) I felt there was a freedom and a sense of self-expression to the carpet that we don’t always see. Sometimes I feel like maybe the celebrities (are) being dressed too much by the designers they’re going with and it’s less about who they are. Whereas I felt (this) was so much a celebration of a community and a love of theater and a love of fashion. And (Lady) Gaga obviously set the tone with her amazing performance art piece.
AP: So it hasn’t become too costumey, as some say?
Wintour: I never think about that. I think of fashion as self-expression, and if everything is simple, elegant good taste, that doesn’t make for individuality and personality. I welcome all the crazy choices everybody makes and that to me is why what happens on the Met carpet is so different. With some of the Hollywood events, everyone is super careful and cautious. This is just about going for it and having a really good time.
AP: You give a lot of advice in this MasterClass. Is there any advice there that stems from some you’ve given to your own daughter?
Wintour: On the contrary, she’s the one that gives me advice! She’s a very determined young lady who’s always had a very clear vision of who she is and what she wants to do. She’s loved theater since she was 8 years old and now she’s working there. But I think it’s very important to understand that you don’t have to make up your mind at 18 or 22. It’s important to try different paths if you’re not sure … it’s testing and trying lots of different things or working with different people and learning from different communities.
AP: If you were speaking to high school seniors, what careers would you suggest they consider?
Wintour: A career that can give you a voice, or (allow you) in some way to be to be helpful. I’ve been exceptionally lucky in that I find myself in a position where through what I do, I can have a voice and I can also be helpful to others.