Anna Wintour revels in her reputation but AMY ODELL reveals she’s a woman of contradictions

Decades before she became an icon, fashion editor Anna Wintour was in New York City, on Lexington Avenue near Bloomingdale’s, wearing a fur coat and high heels, when a mugger snatched her purse. 

Still possessed of the sprinting talent of her youth – once thought to be Olympic-level – even in her heels, she took off after him and grabbed the bag. 

‘The guy didn’t stand a chance,’ says Wintour’s close friend Anne McNally, a former model and ballet dancer who was with her that day decades ago. 

The incident could be a metaphor for Wintour’s extraordinary career. 

Driven, decisive and famously efficient, she has, after more than 30 phenomenally successful years at the helm of American Vogue, long since cemented her place in fashion history. 

With her immaculate bob, signature sunglasses and custom-made designer outfits, she retains, at the age of 72, the power to make and break careers, shape the fortunes of the world’s great fashion houses and influence the entertainment world more broadly. 

Editor-in-chief of American Vogue, Anna Wintour, has cemented her place in fashion history after more than 30 years at the helm of the world's most iconic magazine

Editor-in-chief of American Vogue, Anna Wintour, has cemented her place in fashion history after more than 30 years at the helm of the world’s most iconic magazine

Her work schedule is punishing. 

Rising at 5am and sometimes earlier, she exercises with a personal trainer or plays tennis before having her hair and make-up professionally done and leaving for Vogue’s headquarters at 1 World Trade Center in a chauffeur-driven car. 

Once there, she has no time for small talk, say colleagues. ‘You get two minutes,’ says one. ‘The second is a courtesy.’ 

Editorial meetings, which under her predecessor would last for hours, are over in minutes. 

‘Anna would just go, “Yes, no, yes, no, yes, no. Goodbye,”’ recalls former Vogue colleague Lesley Jane Seymour.

Colleagues marvel at how much Anna can get done in a day: she personally selects the 700 or so guests for the annual Met Gala in New York, which she has planned since 1995, and meticulously supervises the seating plan.

The menus for the event are all approved by her; parsley, garlic, onions and chives were long banned in case they get stuck in guests’ teeth or make their breath smell. 

She also personally approves in advance around 80 per cent of the clothes worn by the mostly A-list attendees. 

Queen Elizabeth II accompanied by Vogue editor Anna Wintour views British designer Richard Quinn's runway show at London Fashion Week in 2018

Queen Elizabeth II accompanied by Vogue editor Anna Wintour views British designer Richard Quinn’s runway show at London Fashion Week in 2018

Hospitality staff, too, are vetted for appearance. ‘God forbid if they’re fat,’ says former Vogue copywriter Sarah Van Sicklen, who helped with the event along with many of her colleagues in the 1990s. 

‘If they are unsightly, they have to go.’ 

During Wintour’s working day, no meal lasts more than 45 minutes. For many years, her regular lunch at the office was a rare steak and mashed potato – she dislikes vegetables – delivered from a nearby hotel and served with a silver fork. 

She would take only a few bites and then say, ‘Take my plate. I’m done,’ recalls former assistant Meredith Asplundh. In recent years, Wintour has occasionally used ‘the diet of cream’ of chocolate milkshakes to make sure she doesn’t get too thin. 

But the ice queen image of her, made famous by The Devil Wears Prada, is not the whole story. 

Friends and colleagues describe Wintour as a ‘complicated’ person full of contradictions, capable of huge kindness alongside her renowned professional ruthlessness. 

‘People misinterpret her focus for coldness,’ says personal friend Emma Soames, who worked for Wintour when she briefly edited British Vogue in the 1980s. 

‘But she’s not cold. She’s generous to a fault. If it did not involve editing Vogue, she didn’t address it. So she had no small talk.’ 

‘She’s been painted as this slightly icy figure. It’s only once you get to know her that you realise she’s not that person whatsoever,’ says Proenza Schouler designer Jack McCollough. 

For the cover of Vogue's May 1989 issue featuring Madonna, editor André Leon Talley said Anna didn't want anything too "bombastic". She chose this simply styled portrait of the then-controversial pop star in the pool

For the cover of Vogue’s May 1989 issue featuring Madonna, editor André Leon Talley said Anna didn’t want anything too “bombastic”. She chose this simply styled portrait of the then-controversial pop star in the pool

Beguiling secrets behind those trademark Wayfarer sunglasses

Wintour’s sunglasses, which seem like an eccentricity, may have a purpose beyond fashion. 

She has claimed her short-sightedness is paired with acute light sensitivity, hence her need for them. 

But Vogue’s longtime West Coast director Lisa Love said she just preferred the appearance of them, which defined her iconic look and added to her mystique. 

Friend Vivienne Lasky remembered Wintour unhappily wearing spectacles when they were at school together, but didn’t recall her wearing sunglasses.

‘I thought it started because if you’re wearing sunglasses, people don’t know they have prescription lenses,’ she said. 

Wintour’s longtime assistant Laurie Schechter recalls that the only thing her highly organised boss seemed unable to keep track of was her prescription Wayfarer sunglasses. Schechter repeatedly had to collect replacement pairs. 

In the mid-1990s, now-disgraced mogul Harvey Weinstein became obsessed with getting Wintour to his screenings, believing that publicity in Vogue would improve his Oscars chances. 

Wintour got a plum seat in the screening room where Miramax publicity staff could monitor her reactions. 

Except that Wintour sat there and watched entire films with her sunglasses on, which made any flicker of a reaction impossible to detect. 

Rumours went around that the sunglasses hid the fact that she was sleeping. 

Weinstein got so frustrated at one point that he told a publicist to ask Wintour to remove her sunglasses. 

Another publicist set him straight. ‘Harvey, you just don’t ask Anna Wintour to take off her sunglasses.

‘There is a person there,’ says her longtime Met Gala planner Stephanie Winston Wolkoff. Wintour has even been seen crying in public on more than one occasion. 

After her then boyfriend Shelby Bryan left the 1999 Met Gala early during their first public date, she was seen leaning against a wall, mascara-laced tears running down her face.

And when the book The Devil Wears Prada, written by her former assistant and clearly based on Wintour, was published in 2003, ‘She wasn’t bothered by it at all’ said Laurie Jones, a close colleague from the time. 

Wintour has, however, been seemingly troubled at times by the dynamic within her high-achieving family. 

Unlike her parents and three siblings, James, Nora and Patrick, she did not go to university, but left school at around 16 to pursue her dream of working in fashion. 

‘I’ve always been a joke in my family,’ she has said. 

‘They’ve always thought I am deeply unserious. In the face of my brothers’ and sister’s academic success, I felt I was rather a failure. They were super-bright, so I guess I worked at being decorative. Most of the time, I was hiding behind my hair and I was paralytically shy. 

‘My sister would always ring up and say: “Where is Anna? Is she at the hairdresser or the dry cleaner’s?” It’s not their world.’ 

Her colleagues would later wonder if Anna Wintour’s astounding career had been partly shaped by a desire to shake off an early sense of ‘failure’, and of being ‘a joke’. 

Unsurprisingly her parents, the renowned Fleet Street editor Charles Wintour and his American wife Nonie, who had met at Cambridge University, were less than happy about their elder daughter’s decision to leave school, though they accepted her decision. 

But while Wintour’s siblings didn’t understand her interest in fashion, her father – known to his employees as ‘chilly Charlie’ due to his forbidding persona – was supportive. 

‘I think my father decided for me that I should work in fashion,’ Wintour has said. ‘I can’t remember what form it was I had to fill out – maybe it was an admissions thing – and at the bottom it said “career objectives”. 

‘And I said, “What shall I do? How shall I fill this out?” So he said, “Well, you write that you want to be editor of Vogue, of course.” And that was it. It was decided.’ 

It would be another 20 years before her father’s vision became a reality.

Anna Wintour and designer Karl Lagerfeld attend the Tribeca Film Festival in New York

Anna Wintour and designer Karl Lagerfeld attend the Tribeca Film Festival in New York

By the time she landed her dream job in 1988, Wintour was 38, the wife of a New York psychiatrist, David Shaffer, and the mother of two young children, Katherine and Charlie – named after her father. 

She knew, in the often cruel corporate environment of Condé Nast, she wouldn’t have long to make her mark. To do so, she learned to take calculated editorial risks. 

On a flight during her first year as editor in chief of Vogue, a man sitting next to Wintour asked her what she did. When she told him, he said: ‘That’s the most incredible publication. It’s so chic. It’s so elegant. It represents everything I think of as being very classic and beautiful. 

‘It’s Katharine Hepburn. It’s Audrey Hepburn. It’s Grace Kelly. It would never be Madonna.’ 

For Wintour, his words were a challenge. 

Madonna was, in early 1989, more controversial than she’d ever been. Her single Like A Prayer, which had come out that March, had led Pepsi to cancel an advert featuring the singer because of objections from religious groups. 

Wintour had little interest in celebrities, but she loved defying expectations – a trait that would shape her editorial decisions over the course of her tenure at Vogue. 

Wintour pictured with her partner Shelby Bryan at a fashion show by Julien McDonald

Wintour pictured with her partner Shelby Bryan at a fashion show by Julien McDonald

She immediately set about ensuring that Madonna would feature on the front cover of Vogue. The star was booked for a shoot in Los Angeles with celebrity favourite Patrick Demarchelier, while a second photographer was hired just to take pictures of Madonna’s house. 

Stars at that time weren’t clamouring – as they later would – for Wintour’s approval. 

‘I’m sure [Madonna] thought she was honouring us as well,’ says former Vogue staffer Maggie Buckley, responsible for booking celebrities. 

The final result was a minimalist image of Madonna in her pool, hair wet and combed back from her face, wearing a simple white swimsuit. 

It was a sensation, with the magazine selling 200,000 more copies than the previous year’s May issue edited by Wintour’s predecessor. 

‘The fact that that very nice man who I sat next to on the plane thought that it would be completely wrong to put Madonna on the cover and completely out of keeping with the tradition of Vogue – being this very classically correct publication – pushed me to break the rules, and had people talking about us in a way that was culturally relevant, important, and controversial,’ said Wintour afterwards. 

That cover helped spell the beginning of the end for supermodels, for so long part of popular culture. 

Interest in them was replaced by a fascination with actresses such as Winona Ryder, who became the new faces of the fashion industry. 

So soon into her job, Wintour’s instincts had been correct, with sales figures revealing that readers loved the new look. 

Three years later, Wintour abandoned an expensively commissioned photoshoot of Cindy Crawford, one of her favourite models, in a swimsuit, which had been intended for the front cover.  ‘We just can’t run it,’ she told staff. The cover that month instead featured a photograph of Princess Diana in Nepal. 

In October 1998, it was Oprah Winfrey’s turn to get the Vogue treatment. 

Wintour pictured with Lagerfeld in 1990, just two years after she took over as editor of American Vogue

Wintour pictured with Lagerfeld in 1990, just two years after she took over as editor of American Vogue

‘Every now and then we encounter a personality who, like many of our readers, wants to do more than just turn the pages. She wants to live the fantasy. She wants a “Vogue make-over”,’ Wintour said in her editor’s letter at the front of the magazine. 

‘The biggest thrill came when we heard that Oprah Winfrey wanted to be made glamorous,’ she continued. 

‘She knew she had to lose weight, but she has done that before, and she promised she would lose 20lb by our deadline. She did.’ 

Wintour was open about her belief that larger bodies did not sync with her vision of Vogue. In 1998, she said: ‘I just felt [Oprah] would look more beautiful 20lb lighter.’ 

Asked how she would feel about a brilliant fashion editor who happened to be 17st, she said: ‘I would have a problem with that.’ 

The Oprah edition was the biggest in Wintour’s editorship, selling 816,000 copies. As Vogue grew, so did Wintour’s own celebrity. 

In 2005, news broke that Meryl Streep would play the Wintour character in The Devil Wears Prada, in a movie version of the book. 

The ‘Twiggy-thin’ regime and Mayfair cut even as a teenager 

Wintour pictured working as fashion assistant at Harpers & Queen in the early seventies

Wintour pictured working as fashion assistant at Harpers & Queen in the early seventies

For teenage Anna Wintour, it wasn’t enough to just look good – she wanted to be admired as the best-dressed person in the room, remembers schoolfriend Vivienne Lasky. 

Her beauty regime, even as a schoolgirl, included regular trips to the Leonard of Mayfair salon in London. 

She also took yeast tablets from the trichologist her father saw to prevent his hair loss. 

The look of the 1960s was skinny. 

‘We wanted to be Twiggy-thin,’ adds Lasky, remembering that she and Wintour ate little more than an apple during the school day. 

Together, the friends queued on Saturday mornings for limited-edition outfits at the hip Kensington boutique Biba. It was there that the teenage Wintour landed her first role in fashion. 

The experience was to be a short-lived one. 

Part of the culture of Biba then was rampant thefts. The absence of a security system, along with the low lighting and busy communal changing rooms, made it easy for customers and staff alike to steal clothes. 

Wintour had been working there just a few weeks when one of her managers was told to let her go because it was believed that she, too, had been taking clothes. 

Her boss certainly didn’t get the impression that Wintour cared about being fired, and she shortly afterwards found work at nearby Harrods.

The film’s director was adamant that he wouldn’t participate in an Anna Wintour hatchet job. 

‘Anna Wintour does extraordinary work and this is going to be a love-letter to working women who do excellent work,’ he said. 

Streep insisted she wasn’t playing Wintour but no matter, she was undeniably the inspiration. The film’s production designer even sneaked into the Vogue building to take pictures of her office in order to replicate it. 

Shortly after Streep signed up for the role, she asked designer Isaac Mizrahi if she was ‘crazy’ to play Wintour and showed him the script. 

Before he read it, he had lunch with Wintour to ensure she wouldn’t feel betrayed if he helped with the movie.

 ‘Anna had the opposite reaction to what I expected. She seemed delighted and told me not to hesitate,’ he recalled in his memoir. 

The film’s director sought advice from other designers but they agreed to do so only under absolute secrecy. 

Naomi Campbell had committed to a role but mysteriously pulled out. Fellow supermodel Gisele Bundchen played the beauty editor role only after clearing the appearance with Vogue. 

Many people in the fashion industry and New York seemingly possessed a deep fear of crossing Wintour. Designers, for example, were terrified to lend clothes to the film’s costume designer. 

Before its public release in 2006, Wintour attended a special screening of The Devil Wears Prada. Naturally, she wore Prada. She sat with her 19- year-old daughter Katherine, who, as the credits rolled, turned to her saying: ‘Mom, they really got you.’ 

The movie’s impact on Wintour’s image was incalculable. She finished 2006 as one of TV host Barbara Walters’s Most Fascinating People, and became a mainstream celebrity, like Cher or Madonna, recognisable by her first name alone. 

This was never her goal, said close friend Anne McNally. ‘She sees it as part of her job. She’s very conscious that this is a persona that exists at the moment because she has that job, and the minute she doesn’t have it, she knows it’s going to be different.’ 

For now, though, celebrities must be comfortable company for Wintour. Like her, they understand the burdens and advantages of having power, money and a busy travel schedule, and therefore little time for friendly socialising. 

She knows how they should be treated, and exactly what they expect. 

At one Met Gala, George and Amal Clooney requested – and were given – a private bar so they could have a drink away from the other (lesser?) A-list celebrities. 

The Metropolitan Museum of Art also had its bookshop fitted with upmarket rental furniture for Amal, so she had a private place to change clothes. 

The only person Wintour couldn’t bend to her will was Beyonce, who appeared on the September 2015 cover of Vogue, and insisted on directing her own cover shoot video.

Given her her immense success and discipline, it is hard to imagine life being a struggle for Anna Wintour. Yet her arrival in the US had been far from seamless. 

At the age of 25, she had given up her job as a fashion assistant at Harpers & Queen magazine in London and moved to New York, which Soames said she believed to be the ‘centre of the universe’. 

There, she landed a role at Vogue rival Harper’s Bazaar. She had no idea how difficult life in America would be. Back in London, her creativity and ideas had mattered. On an American magazine, the hierarchy was entirely different. 

Although responsible for the fashion shoots, others decided on the clothes, the models and the photographers. She was not required to stamp her vision on anything. It was, as she later admitted, a ‘disaster’. 

After just nine months, despite her American colleagues loving her personal style, her work ethic and above all her posh British accent, she was fired for, she later said, being ‘too European’.

Wintour was longtime friends with Chanel creative director Karl Lagerfeld and was said to have been distraught when he died in February 2019 aged 85

Wintour was longtime friends with Chanel creative director Karl Lagerfeld and was said to have been distraught when he died in February 2019 aged 85

More disappointment followed. During her hunt for work, she visited the offices of Interview, a pop magazine set up by Andy Warhol, to show the editor an idea she had been working on. 

‘He just looked at it for one second and said it was trash and she started crying,’ Warhol wrote in his diary. 

‘She’s such a tough cookie I could never imagine her crying. I guess it was her femininity coming out.’ 

But Wintour was not about to give up. She was still trying to prove herself to her intellectual and academic family – perhaps most especially her father. 

A month later, Warhol saw Wintour having dinner at an Italian restaurant and wondered if he had made a mistake. 

‘Maybe we should have [hired her],’ Warhol wrote. ‘We do need a fashion person, but I don’t think she knows how to dress. She’s actually a terrible dresser.’ 

To add to Wintour’s worries, her parents’ marriage, which had long been in trouble, fell apart shortly after she lost her job at Harper’s Bazaar. 

Her mother, who had for the whole of their 36-year relationship dealt with her husband’s wandering eye, was grief-stricken. 

Their divorce seemed difficult for their daughter, too, say friends. Her luck finally changed when a feature she had written for New York Magazine about art and fashion caught the eye of Vogue’s editorial director Alexander Liberman. 

A sculptor in his spare time, Liberman was enchanted by Wintour. Here was a sophisticated, young European, beautiful and impeccably groomed and styled – the physical embodiment of fashion – who shared his interest in art and a devotion to bringing it to the printed page. 

Feeling Vogue needed a shakeup, he offered her the role of creative director. Former colleague Corky Pollan remembers overhearing Wintour excitedly phoning her father in London to tell him the news. 

But it sounded to Pollan as though his response was negative. 

‘Well, they think I can do it,’ Wintour told her father. It sounded as if she was on the verge of tears. But she had arrived. 

Five years later, she became editor-in-chief of American Vogue – and the undisputed queen of the fashion world.

Wintour’s relationship with her father, who died in 1999, had been complicated. She adored, admired, and emulated him, but was scarred by his infidelity. 

He had opened the world of publishing to her and took her interest in fashion seriously. 

Her famous persona and editorial instincts were very much a product of being Charles Wintour’s daughter, and now that staggeringly powerful influence was gone. 

She would talk about his accomplishments and impact on her for the rest of her career. 

In 2019, she told an interviewer: ‘It was so inspiring growing up in a house full of journalists and editors and always being aware of what was happening in the world. It made me love the news and it made me love culture. It was all around us and he brought what he did home and those kinds of people – politicians, editors – they were at the house at all times. And how lucky was I?’ 

Her defence of her father’s character against those who emphasised his frosty demeanour was perhaps partly in defence of herself – maybe even her way of keepng his memory alive. 

In his will, her father wrote: ‘I DO NOT leave a share in my residuary estate to my daughter ANNA WINTOUR SHAFFER, as she is well provided for, but I wish her to know that I am very proud of her great success and achievement and I am equally pleased that she has combined her career so happily with her family life.’ 

For Anna Wintour, there can surely have been no greater, nor more welcome, validation.

  • Adapted from Anna: The Biography, by Amy Odell, published by Atlantic on May 5 at £20. © Amy Odell 2022. To order a copy for £18, go to mailshop.co.uk/books or call 020 3176 2937. UK p&p free on orders over £20 until May 14.


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