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Anna Wintour
Chief Content Officer (Condé Nast) and Global Editorial Director, Vogue, Condé Nast

Anna Wintour: Life After Vogue

📅 Dec 08, 2025 The Rest Is Politics: Leading and The Rest Is Politics 70 MIN 154089 VIEWS 86 SEGMENTS · 4 SPEAKERS
Watch AD FREE here:    • AD FREE: Anna Wintour: Culture, Influence,...   Why should everybody get fired at least once? As the former Editor-in-chief of American Vogue, how does Anna Wintour use fashion as a cultural and economic force? Why is Anna’s leadership style defined by the speed of her decision making? Rory and Alastair are joined by Fashion icon Anna Wintour to answer all this and more. ------------------------------------------------------------- For Leading listeners, there’s free access to the Wordsmith Academy - plus their report on the future of legal skills. Visit https://ww...

Questions asked in this interview

12
  1. 0:00What does Trump have to do to get back on the invite list or is he off for good?
  2. 32:04So does any of that happen in fashion or is fashion a complete exception to what's happening in the broader political cultural world?
  3. 38:52They are celebratory. How does that work?
  4. 43:48Do you worry about losing readers?
  5. 44:43How difficult is that with the current president?
  6. 45:42What's your feeling about the state of media and politics?
  7. 46:28Do you like the golden oval office?
  8. 46:51Did you ever think you'd had enough?
  9. 47:56What is the less nice bit of being famous?
  10. 52:40Was that a step too far on the celebratory side?
  11. 53:17Why have you never written a memoir? Will you ever?
  12. 57:38What does Trump have to do to get back on the invite list? Is he off for good?
Alistair Campbell 0:00 ↗
on the Met. What does Trump have to do to get back on the invite list or is he off for good?
Anna Wintour 0:08 ↗
Thank you for having me. [laughter]
Narrator 0:14 ↗
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Rory Stewart 1:38 ↗
Welcome to the rest of this politics leading with me Rory Stewart
Alistair Campbell 1:39 ↗
and me Alistair Campbell. And I have to say, I don't think I've ever seen our young, mainly female production team quite as excited as they were when we told them that you'd agreed to come on. We are talking to fashion icon Anna Wintour. I interviewed Anna about 10 years ago for my book, Winners and How They Succeed. And I thought I was going to put her in the section on innovation, but I ended up making her my main profile on leadership because in a way she's the leader not just of a very famous magazine, but of an industry. And that's certainly how she's seen. And the maker of a documentary about her once said, 'You can become famous in Hollywood without Steven Spielberg's blessing. You can become famous in software without Bill Gates' blessing, but you can't succeed in fashion without Anna Wintour's blessing. She was born in London, which is where we are now. She revisited her old school yesterday. Her dad was a very famous newspaper editor. She left school at 16. Pretty determined to make it big in journalism and in fashion. Editor of British Vogue by her mid-30s and editor of the job she'd always wanted, editor-in-chief of American Vogue and artistic director of Condé Nast before she hit 40. Still a very big deal in Condé Nast, but this is a job she did from 1988 when Rihanna was born, Adele was born, Emma Stone was born to 2025. So I've worked out this is 1,300 Scaramucci almost as we call them. And she's still a very very big cultural figure and we're absolutely delighted that you're here.
Anna Wintour 3:32 ↗
Thank you Alistair. Thank you Alistair. It was actually quite the opposite of what we're doing today going back to my old school North London Collegiate. And I hadn't been since I left. I think it was a bit younger than 16. But it was incredible to see the change because when I went there, it was sort of Dickensian conditions where I remember thinking of every possible excuse not to go swimming outdoors in a freezing pool and sitting endlessly on the tube to Stanmore. They now have a incredibly diverse student body about 700 girls perfectly dressed in incredibly chic tracksuits and they had a cappuccino bar which was very welcome as it was quite early in the morning. [laughter]
Alistair Campbell 4:21 ↗
Anna, can we bring you back to that moment? I think it's a lovely route through. You grew up in a very different world. Your mother came from a well-established American family. I think your grandfather was possibly a general. Is that right?
Rory Stewart 5:16 ↗
Amazing. So there's that whole story of an extraordinary athlete law professor, but on the other side we have the two different bits of British establishment presumably your British grandfather who was a major general who fought in the first world war would have represented a world that passed. I mean the world in which he was born would have been the world of Queen Victoria, the world of the British Empire, went through this crushing experience of two world wars and then your father worked with this legendary figure Lord Beaverbrook again who's a sort of part of the world of Winston Churchill. So, is that a part of your family you've been interested in?
Alistair Campbell 7:50 ↗
Tell us a little bit about this. What did you learn from your father's style and what positive and what negative lessons you took? What's the difference between the way you edit and the way he edited?
Rory Stewart 9:32 ↗
And I couldn't help thinking of that whether it's partly that sort of tennis approach to life as opposed to any other sport I can think of.
Alistair Campbell 10:46 ↗
How would you define your leadership style?
But you mentioned Chilly Charlie as your dad's reputation. I mean, you've had worse nicknames than that.
Rory Stewart 12:03 ↗
Famously, you were a bit like the queen used to say, just don't get involved if people say bad things about you. But what's your analysis of the difference between who you are and the kind of image which is very powerful?
Alistair Campbell 13:40 ↗
And how did you learn to cope with attacks and abuse? You're a very high-profile figure and as you say, people accuse you of being nuclear winter or people would have watched The Devil Wears Prada and the whole mythology is some of it negative. And maybe if I come back to your father, how would he have coped with people being very rude about him? How did he think about people being critical or rude about him?
Rory Stewart 14:57 ↗
And maybe this connects to Alistair. I'd like to bring Alistair in on this. So you talked a lot about decisiveness as a way of leading. And in Alistair's book he's very interested in this. You're making decisions very quickly. And I guess some of those decisions will be wrong, some will be right, but the merit of them is they're being made fast.
Alistair Campbell 17:28 ↗
You said when we met 10 years ago, one of the quotes that really leapt out at me, you said, 'I'm not creative at all.'
What does that mean?
American Vogue, you're running the show.
So what do you define as having a vision? Because I think that's your strength. You know what you want to do. It was a very different time as we've discussed back then and they had these covers on American Vogue that were very 80s with big hair, big earrings, big smiles, and they were nearly always blonde and photographed by the great Richard Avedon. So I arrived, working with Alex, and we did a cover with Dick that was very similar. Then a shoot came in that we had commissioned on Paris Couture and it was girls walking in the street, nothing earthshattering but different for American Vogue. The picture came in of this amazing girl named Michaela. She had on a Lacoste t-shirt with a big jeweled cross and Guess jeans, and you could see shockingly a little bit of stomach. I just looked at that image and thought, this should be the cover. It signified change, modernity. The publishers rang up and asked if it was a mistake, and today it's the cover people talk about most because it became such an iconic symbol of a different kind of
well just a different attitude, cultural shift
Rory Stewart 21:03 ↗
One of the things that is amazing is that we often think the world today is completely different from the world of the late '80s, early '90s when you took over Vogue because of social media and the transformation of television and newspapers. And yet there's a continuity. The world isn't quite as radically different as one might expect. Some of the things we might say about fashion, influences, image, narrative, you could have said about the late '80s, early '90s. Is that right?
Final one for me, then back to Alistair. What's an example of a silly idea? What sort of thing slightly irritates you but often happens?
Alistair Campbell 24:00 ↗
But are there things you've learned over decades to reject as a category of suggestions when a brilliant young person comes to you and says, 'Anna, what we need to do is this,' where you tend to think you've learned enough to know that kind of idea doesn't really work?
Rory Stewart 25:48 ↗
Okay, Anna, Alistair, quick break and then back for more.
Narrator 25:55 ↗
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Rory Stewart 27:14 ↗
Was there a point at which you sensed or realized that you as an individual were becoming a brand in your own right? Was that something you wanted to happen like something you buy at the supermarket?
No. What did you- but you know what I mean? You become known as Anna. You are a brand. You have the look, the glasses, the hair, you have the
But that wasn't inevitable that the editor-in-chief of American Vogue takes that role. You developed that role. Was that deliberate or did it just evolve?
Alistair Campbell 29:26 ↗
Tell our listeners and viewers why fashion matters beyond the obvious.
Rory Stewart 32:04 ↗
There's something very interesting listening to you, which is a sense of authority and optimism. You represent a consensus about what high fashion is and you have a confident view in the way it contributes to society. That isn't true about politics. Politics has gone from a centrist world when you were beginning at American Vogue, with Bill Clinton, Tony Blair, where votes were in the center, newspapers were huge, only four channels in the US, everybody watched Walter Cronkite or the Dimblebees in Britain, and there was a sense of authority and optimism. That's all collapsed. Politics is now polarized. And part of that is social media. There are no longer news anchors that tell you how to think. You've got a million different views on TikTok. We're all confused, depressed, fragmented. So does any of that happen in fashion or is fashion a complete exception to what's happening in the broader political cultural world?
Alistair Campbell 36:35 ↗
Just sticking with the optimism point. You've already mentioned that you were fired more than once. You once said that everybody should get fired at some
Anna Wintour 36:46 ↗
Point. Was it just maybe more? I can't remember anymore.
Alistair Campbell 36:49 ↗
Well, you moved on. You moved on a few times. But you said once that everybody should get fired at some point.
Anna Wintour 36:56 ↗
Yeah.
Alistair Campbell 36:57 ↗
You were a great believer in setback and something else you said.
Rory Stewart 37:00 ↗
When we met, which I thought was really interesting, you said we never have postmortems.
Anna Wintour 37:04 ↗
We do actually, that's not completely true. I think challenges are amazing. When I was fired from Harper's Bazaar they told me I would never understand the American market. I was lucky enough to go and watch...
Alistair Campbell 37:19 ↗
Does that fire you up?
Anna Wintour 37:19 ↗
I thought they were probably right. I hadn't been in New York long and I can't remember the shoot that was so controversial, but it was great for me because I ended up at New York Magazine working for Ed Kosner. He gave me a free hand and taught me a lot.
Rory Stewart 38:52 ↗
One thing I was looking at your November issue. The interviews are not like the snarky interviews in British newspapers. They are celebratory. How does that work?
Anna Wintour 39:43 ↗
For Vogue, if we put somebody on the cover, we are celebrating them. We're not looking for a takedown. That's a conscious decision. Our job is to celebrate people who excel, not to be negative.
Rory Stewart 41:53 ↗
Another famous cover was Hillary Clinton. I read that on the day she lost the election, you addressed the staff in tears.
Anna Wintour 42:24 ↗
We have a history of profiling first ladies. Hillary is a remarkable woman and a personal mentor. She deserved to be celebrated during that difficult time.
Alistair Campbell 43:48 ↗
Do you have to be careful about being critical of Trump? Do you worry about losing readers?
Anna Wintour 44:07 ↗
It's a polarized situation, but I separate my role at Condé Nast from my advocacy for the fashion industry. I've advocated on tariffs with the White House and with UK ministers.
Rory Stewart 44:43 ↗
Obama said you're one of the best fundraisers going because you don't bring baggage. Are you out as a Democrat? How difficult is that with the current president?
Anna Wintour 45:06 ↗
There were excellent election results recently. It was ironic to hear Secretary Duffy urge politeness the same week the president called a journalist piggy and ugly. They need to connect their messaging.

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APA

Wintour, A. (2025, December 8). Anna Wintour: Life After Vogue [Interview transcript]. The Rest Is Politics: Leading and The Rest Is Politics. CEOInterviews.AI. https://ceointerviews.ai/interview/1027904/

MLA

Anna Wintour. "Anna Wintour: Life After Vogue." The Rest Is Politics: Leading and The Rest Is Politics, 8 Dec. 2025. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/1027904/.

BibTeX
@misc{wintour2025_1027904,
  author       = {Anna Wintour},
  title        = {Anna Wintour: Life After Vogue},
  howpublished = {Interview transcript, The Rest Is Politics: Leading and The Rest Is Politics. CEOInterviews.AI},
  year         = {2025},
  month        = {dec},
  url          = {https://ceointerviews.ai/interview/1027904/},
  note         = {Speaker-attributed transcript with timestamps}
}