Part I: André Leon Talley's 'Anna' Interviews

Before he died, the late fashion icon shared his memories about Anna Wintour and his thoughts on her legacy.

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When I first reached out to the late André Leon Talley to request an interview for my book ANNA: The Biography, he was unsure if he wanted to speak to me. Talley’s relationship with Anna Wintour began in the early eighties, when they both were just starting at American Vogue under Anna’s predecessor as editor-in-chief Grace Mirabella. Talley went on to become Vogue’s creative director when Anna became editor-in-chief in 1988, left the magazine briefly in the nineties, and then returned to work for many years as contributing editor. By the time I reached out, he had had a public falling-out with Anna.

Months went by before he emailed me to say he had decided he would speak to me. We had long phone conversations in March and April of last year. He was generous with his memories and surprisingly admiring of Anna, given that he had not long before been in the press calling her “a colonial broad.” Their relationship had perhaps never been entirely easy or straightforward to Talley, despite how close he felt to her. A turning point for him was not being asked to host the red carpet livestream at the 2019 camp-themed Met Gala – a role he had held for years – and never getting a call from Anna or anyone else at Vogue to tell him (he was replaced with a YouTuber). Yet he told me in April of last year, “I still love Anna deeply.” He added, “To this day, I still want the approval and the admiration and the acceptance of Anna Wintour. I mean, I really do want that, and I say that to you and for your book – I've never said it to anyone else.”

Talley died on January 18 at age 73. We won’t get to hear from him again, but he had a wealth of knowledge and insight about both fashion broadly and the woman who has led it for 34 years. This is an edited, condensed version of our interviews.

When you first started at Vogue and Anna was creative director, seemingly planted there by management to train for Grace Mirabella’s job, did you sense tension between the two of them?

Well, there was always tension between her and Grace. She wanted Grace Mirabella's job, she wanted to be editor-in-chief. I often went to Anna as the person who kept me under her wing when things were rejected by Grace. She said, “Don't worry about it, it'll be fine, I'm going to pass this story forward to Mrs. Mirabella.”

I’ve been told that with Grace there was a lot of hemming and hawing.

Picture it – New York Fashion Week, end of the week — Friday, Saturday morning in the offices of Grace Mirabella. The whole staff — Anna Wintour, myself, Polly Mellen, all the other editors, the fur editor, the fabric editors, discussing the fashion week – 8 o'clock, 12 o'clock, 1 o'clock, 2 o'clock, 3 o'clock, 4 o'clock. We're still pouring over slides [of images from fashion shows], not really getting anything resolved, just pausing and reflecting and having think tanks about them. Several editors could be on the slide box at the same time discussing perhaps, say, one design – Bill Blass as opposed to Geoffrey Beene as opposed to Oscar de la Renta. We'd go in there around 9, we'd leave at 4:30, no decision made.

When you were in those meetings and Anna was there, if you had looked at her, what would her expression have been? What would you have seen?

The same as it is today. Like the eternal sphinx in Egypt where you cannot read what she's thinking. The emotions are not signaled on her face, the bob is framing the face, and legs are crossed. She never showed her thoughts. Never. To this day, I think that was one of her strengths is that you never can guess what she's thinking.

Anna’s management style as editor-in-chief was very different from Grace Mirabella’s.

With Anna Wintour, you have a story board, it's all worked out on paper, and this is the display, and this is what we want, and blah, blah, blah. And you get it done right or if you don't get it right, you get to do it again. With Anna, it was very succinct. Anna did not sit around discussing models or fashion or features. That was not her thing. She edited in sort of a self-isolated bubble, but she would call you in if you had a specific assignment.

When Anna left American Vogue to become editor-in-chief of British Vogue in 1986, she asked you to go to London and work for her, but you said no.

Anna can take any kind of a decision and it's water off the back of the duck. So I didn’t go. And I'd go to London and see the collections, she'd have me in her office and asked me what did I think about the fashion shows. We were still very close friends.

What would those conversations be like?

It'd be very brief. I can't remember distinct conversations. We would just have conversations about, “What do you think of this layout?” And I'd say, “Oh it looks lovely.” I didn't have any great criticism because at that time, I was not that confident about my judgment with Anna. I was very aware of who she was and I was aware of who I was, but I was certainly aware that she was becoming the most important woman in fashion. Particularly when we went to the collections in Europe, people responded to her. She didn't hang out with the young designers, nor did I, like Claude Montana, Thierry Mugler. But she really had a hold on the power players, like [Karl] Lagerfeld, Mr. Armani – that kind of a designer, you know? They liked her a lot. And she knew how to charm her way into their inner sanctums.

Her impact was star power based on her persona. And her persona was meticulously, meticulously articulated, with the great strength of style, fitness, grooming to a fault, grooming without mistakes, no mistakes in her dress, no mistakes in her shoes, no mistakes in the clothes she wore, even when she was wearing Geoffrey Beene. Sometimes I did not like her Geoffrey Beene choices, I did not like them at all, but at one point was wearing a lot of Geoffrey Beene. And in those days she was not wearing Manolo, she was wearing Susan Bennis/Warren Edwards and Maude Frizon. Then she got married and she moved to Chanel.

How would you say her personal style evolved over the years?

Her style has never changed. Her style is based first on her own look, which is the Louise Brooks bob, I remember she had [it] in ‘83 [when we started working together at Vogue]. It was more dramatic. Now it's very normal and it's always based on a silhouette. She does not change her style. She's gone to all these Met Galas with mostly Chanel dresses. That is her template. Her day dresses are usually by Prada, and they are specifically worked out with Miuccia Prada, they are usually prints. In the last couple of years, she's worn longer dresses, which, I don't know why she wears them, but before she was wearing shorter dresses. She does not go for anything that looks excessive on her. She never wears a strapless dress ever. She wears very little jewelry. I've never seen her with an earring on. She does wear diamond watches, sometimes a ring. Her style is based on those three necklaces, the triplicate of necklaces, which are 19th century aquamarines and semi-precious stones from England. She's rarely worn pants. In the beginning she did wear trousers, particularly Marni pantsuits. She likes minimalism. You'll never see a big sweeping skirt. You always see her in slim silhouette. Her sandals are always the same Manolo Blahniks. It's a very set style. And it gives her confidence, the hairdo gives her confidence. She doesn't have to think about it. It's like a man's uniform.

Did she ever talk to you about changing her hair?

Never. Some people think it's a wig, it's certainly not a wig. I said, are you crazy? She doesn't wear a wig. It's done in 15 minutes. She doesn't have time to waste. She washes it and they blow dry it and it's done.

You’ve talked about going to fittings with Anna. When did you start doing that?

From 2000 until 2018, I went to almost every Chanel fitting, be it in New York or Paris. Always with Chanel because I was close friends to Karl [Lagerfeld], so she knew that I knew what Karl was thinking. Let me tell you this – sincere joy. This was not considered a slap in the face. It was not considered that I was inappropriately asked to do this. I felt it was an honor to attend her fittings. It was my moral duty.

I remember the last fitting I ever went to with Anna was in the new Vogue fashion closet downtown in One World Trade Center, that beautiful pale pink dress she wore to the exhibit called Notes on Camp with the pink feathered cape. She would not want me to reveal this, but you are writing a book about her – sometimes there'd be four or five fittings, and that's because she cares about the way she looked in her clothes. Anna also goes to bed early and gets up – the fitting would call for 8:30, and she’d be at the Chanel headquarters at 7:45.

So Chanel comes to her?

She'd maybe select the dress in Paris in January or July. And then they would come to New York to fit the dress and while they were in New York, they would fit other clients as well. They would sometimes come two or three times when she was having dresses made for the Met Ball.

Anna is said to have advised powerful people like Hillary Clinton on her wardrobe. Do you know anything about that?

Well, I don't know about that. It did seem like it was on the radar, but Anna kept everything separate from other things. She did not talk about what she was doing. She kept everything locked up in a compartment.

That’s what makes her a tricky subject for me.

That's what makes her tricky for everyone who works for her. You didn't know where you were sometimes. And that's cause of frustration. Because Anna did not like to explain and did not like to have confrontations.

So many people have said that, which is interesting because I think people think of her as confrontational.

She is not at all. She did not like confrontation whatsoever.

Do you think there is a deep, warm person beneath the famous façade?

I think that she is a deep warm person when she feels that it's necessary to be deep and warm. Only very few people are privy to that. Her children, [close] friends. And she can be intimidating. Like we would go to resort shows, and you would go to several designers’ studios. If the resort show was called for a 7:30 appointment, well that's early for most people to get up and be in an appointment at 7:30 am, ok? Maybe they do it on Wall Street, I don't know. But the meeting was at 7:30, you'd better be there at 6:45, because most likely Anna has arrived at 6:50 and the meeting is over by 7:10.

What are her pet peeves?

It really piques her when you're late. Or when you don't show up and she expects to see you there, she gets really, really upset. She can't stand absentia or tardiness. She can't stand people who linger over their food. My first lunch with Anna when we first went to Vogue was at BiCE. We sat down at 1 o'clock, the lunch was over at 1:12. As I was about to bite into my main course [she said], “OK, we're done. Let's go back to the office.”

Did she eat lunch?

She ate pieces of avocado and prosciutto. I know she loves prosciutto and avocado. Dinner can be steak beurre and fingerling potatoes, roasted, a glass of white wine. I didn’t see her enjoying anything like pasta. And no desserts ever.

Read Part II of my interviews with Talley here. If you haven’t yet, don’t forget to subscribe.