Daily haircuts and a 'weird' go-to lunch: Inside Anna Wintour's complicated, private world.

With her trademark sleek bob haircut and dark Chanel sunglasses, Anna Wintour is undoubtedly the most recognisable figure in the fashion industry.

The 74-year-old British-American, who has been at the helm of Vogue since 1988, has been a prominent figure in fashion for decades. And par for the course when you're one of the greatest minds in fashion of all time is a tendency to develop a rather specific set of preferences — including a strict hair styling regimen and a go-to lunch demanded every single day.

Although rumours about Wintour's departure from the iconic magazine have been brewing for more than a decade, it seems the fashion mogul has no plans to go anywhere anytime soon.

Anna Wintour’s easy-to-follow advice on what to wear to a job interview. Post continues below.

Anna Wintour's career.

Wintour first became involved with the fashion industry at the age of 15, when she began working at the influential Biba boutique. The role was arranged by Wintour's father, Charles, who was the editor of London's Evening Standard from 1959 to 1976.

Wintour's mother, Eleanor Baker, was an American social worker. The 74-year-old has four siblings: Patrick, James, Nora, and Gerald, who died in a car accident as a child.

"I think my father really decided for me that I should work in fashion," Wintour recalled in documentary The September Issue.

After a brief stint in fashion, Wintour's career in fashion journalism began in 1970 when she was hired as an editorial assistant at Harper's & Queen – the merge of publications Harper's Bazaar UK and Queen. At the time, she reportedly told her co-workers that she hoped to one day edit Vogue.

After several years at the publication, Wintour moved to New York City with her boyfriend, freelance journalist Jon Bradshaw. In the new city, Wintour became a junior editor at Harper's Bazaar in 1975, before landing her first position as a fashion editor at Viva.

After Viva was shut down, Wintour spent two years travelling between New York and Paris, while starting a new relationship with French record producer Michel Esteban.

Anna Wintour in 1990. Image: Getty.

When she returned to work, Wintour briefly took on a role as the fashion editor of Savvy and New York, before setting her sights on Vogue. 

At first, Wintour was hired as the magazine's creative director, before becoming the editor of the UK edition of Vogue. Almost immediately, Wintour's new role landed her the now-infamous nickname of 'Nuclear Wintour'.

Upon taking over the editorship, she made dramatic changes, replacing many of the staff at the magazine. Responding to the 'Nuclear Wintour' nickname, which was coined by her staff, Wintour told 60 Minutes, "If I'm such a bitch then they must really be a glutton for punishment, because they're still here.

"If one comes across as sometimes being cold or brusque, it's simply because I'm striving for the best."

Just months later, Wintour became the editor of US Vogue. When the first magazine under Wintour's helm went to print, the printers famously called the Vogue office to check that they had the correct cover. Unlike previous covers of the publication, which predominately featured tight headshots of well-known models, Wintour used 19-year-old model Michaela Bercu in a $10,000 jacket and a $50 pair of washed-out jeans.

Image: Vogue.

It was the first time a cover model on Vogue had ever been seen wearing jeans – a decision made as Bercu was pregnant and couldn't fit into the original skirt that she was meant to wear on the cover.

"It was so unlike the studied and elegant close-ups that were typical of Vogue's covers back then, with tonnes of makeup and major jewellery. This one broke all the rules. Michaela wasn't looking at you, and worse, she had her eyes almost closed. Her hair was blowing across her face. It looked easy, casual, a moment that had been snapped on the street, which it had been, and which was the whole point," Wintour recalled in 2012 in an article in Vogue.

"Afterwards, in the way that these things can happen, people applied all sorts of interpretations: It was about mixing high and low, Michaela was pregnant, it was a religious statement. But none of these things was true. I had just looked at that picture and sensed the winds of change. And you can't ask for more from a cover image than that."

The cover still remains Wintour's favourite to this day.

In another new change, Wintour began shifting towards using celebrities including Madonna on the cover of the magazine.

"The supermodels led us to celebrity," she told The Guardian. 

"The generation of models who came after the supers just wanted to be models, and didn't want that spotlight. Meanwhile, celebrities were starting to engage with fashion, realising the power of fashion to build their personality, to express who they were, on the red carpet or in the front row. So the supermodels ended up being replaced by celebrities."

Image: Vogue.

Anna Wintour's famous friendships.

Over the years, Wintour has become well known for her famous friendships. The Vogue editor-in-chief is often spotted in the front row at fashion shows alongside the likes of Bradley Cooper, David and Victoria Beckham, and Kate Moss.

She's also close friends with tennis champion Roger Federer. In August 2018, Federer, his wife Mikra, and their twins, visited Wintour's Long Island summerhouse for a Federer-Wintour family tennis tournament.

"It was the best gift a daughter could give a tennis-mad mother," she told The Guardian. "I got to play doubles with Roger for the first time in our very long friendship, against my two nephews."

Anna Wintour and Roger Federer. Image: Getty.

Anna Wintour's relationships and family life.

As for Wintour's relationships, the British-American married David Shaffer, a child psychiatrist and an older acquaintance from London, in 1984. Together, the couple had two children – son Charles and daughter Bee.

Wintour and Shaffer divorced in 1999, and Wintour went on to marry American telecommunications pioneer Shelby Bryan, whom she met at a charity ball while they were both married. In the years since, Wintour has very rarely opened up about her private life.

"There are certain things that no one wants to read about in the tabloid press," she told New York magazine back in 1999.

"You know that your friends and your family have one vision, and if the outside world has another, then that's just something that you just don't focus on."

Shelby Bryan and Anna Wintour in 2011. Image: Getty.

Bryan, a prominent Democratic Party fundraiser, agreed, telling Texas Monthly: "There's an old-fashioned view that your personal life should be kept private, and that's my view."

Now, Wintour's daughter Bee, who previously worked as a producer on Late Night with Seth Meyers, often appears on the red carpet alongside her mother.

Bee Shaffer and Anna Wintour in 2019. Image: Getty.

Bee, now 36 years old, married Francesco Carozzini, the son of late Vogue Italia editor-in-chief Franca Sozzani, in 2018. Wintour's son Charles married Elizabeth Cordry in 2014, and the couple welcomed a daughter in 2017.

Anna Wintour's personal life and criticism.

In interviews over the years, Wintour has opened up about her daily routine.

The Vogue editor-in-chief generally rises around 5am before either playing tennis or doing a workout. On workdays, she will generally arrive at work at Vogue's offices in Manhattan around 8am.

Since 2016, hairstylist Andreas Anastasis has been part of maintaining Wintour's iconic hairstyle.  Aside from getting a professional blow dry every morning and evening, Wintour also gets help from Anastasis, who arrives at her townhouse in Greenwich Village, monitors and then carries out anything that needs doing regarding her bob. 

This includes cutting, colouring, spraying, blow-drying or styling (yes, that means a daily trim), per The New York Times.

Since taking the helm at Vogue, Wintour has often been described as being emotionally distant — and according to the documentary Boss Woman, Wintour reportedly rarely remains at parties for longer than 20 minutes.

"At some stage in her career, Anna Wintour stopped being Anna Wintour and became 'Anna Wintour', at which point, like wings of a stately home, she closed off large sections of her personality to the public," The Guardian wrote in 2006.

Similarly, a friend told the Observer that Wintour can be "very terse".

"I think she has been very rude to a lot of people in the past on her way up – very terse," she said.

There have long been rumours about unwritten rules imposed by the editor, including allegedly forbidding junior staff from initiating conversation with her. "You definitely did not ride the elevator with her," one former assistant said.

The 74-year-old has also been publicly criticised – and even physically attacked – by animal activists due to her pro-fur stance. Despite the attacks, Wintour continues to wear fur, feature fur in Vogue, and refuses to run paid advertisements from animal rights organisations.

Criticism of Wintour often stems from her reportedly "elitist" views of femininity and beauty.

Romeo Beckham, Cruz Beckham, David Beckham, Harper Beckham and Anna Wintour. Image: Getty.

According to former writers at the magazine, Wintour has been known to exclude "ordinary women" from the publication.

"She's obsessed only about reflecting the aspirations of a certain class of reader," a former writer for the magazine told Slate in 2006. "We once had a piece about breast cancer which started with an airline stewardess, but she wouldn't have a stewardess in the magazine so we had to go and look for a high-flying businesswoman who'd had cancer."

The Devil Wears Prada.

In 2003, Lauren Weisberger, a former assistant to Wintour, released The Devil Wears Prada.

The book, which follows a young woman hired as an assistant to powerful fashion magazine editor Miranda Priestly, was loosely based on Weisberger's experience working for Wintour.

"It wasn't a one-to-one portrayal," Weisberger told Daily Mail in 2010. "But of course, my time at Vogue informed the book, there's no denying that."

A film adaptation of the book was released in mid-2006, with Meryl Streep playing Miranda Priestly. When asked about the film, Wintour told 60 Minutes: "It was entertainment. It was not a true rendition of what happens within the magazine."

One thing that the movie certainly did get right was Wintour's particularity when it comes to food. In one scene in The Devil Wears Prada, Miranda Priestly demands a costly torte filled with warm rhubarb compote (and not dacquoise) for lunch.

Of course, she doesn't eat it... nor does she ask for it again. 

But in Anna: The Biography, Amy Odell wrote that the editor-in-chief has her own very specific lunch order: steak and a Caprese salad, minus the tomatoes.

According to New York Post, it costs about $116. 

Meryl Streep as Miranda Priestly in The Devil Wears Prada. Image: IMDB.

Andre Leon Talley's memoir.

For decades, American fashion journalist Andre Leon Talley had been Anna Wintour's right-hand man. In his memoir, however, Talley has made it clear that the pair are no longer friends.

According to MailOnline, Talley wrote that Wintour is "ruthless" and "not capable of simple kindness".

"She is immune to anyone other than the powerful and famous people who populate the pages of Vogue," he wrote. "She has mercilessly made her best friends people who are the highest in their chosen fields."

In the book, Graydon Carter, the former editor of Vanity Fair, agreed with Talley's comments.

"One day she treats me like a good friend and a colleague, and the next day, she treats me as if she had just handed over her keys to an unknown parking valet," he said.

This article was originally published on April 27, 2020 and was updated on May 6, 2024.

Feature Image: Getty.