During a disagreement about a fashion shoot, the Italian photographer Oliviero Toscani remembered telling Anna Wintour: ‘Listen, Anna. I think you need a shrink.’
A few weeks later she phoned him. ‘I found a shrink,’ she said. ‘And I’m going to marry him.’
Wintour had met the academic David Shaffer during a get-together at the home of friends in New York. Thirteen years older than her, he had moved from London to the U.S. to become chair of child psychiatry at Columbia University.
He was single, but Anna was living with her journalist boyfriend Michael Stone when overtures began.
‘Michael would send flowers. David would send flowers. Daily. Daily,’ remembers Laurie Schechter, an early assistant.
There were also phone calls from Shaffer, followed by Wintour heading ‘out for lunch’ from the office only to return ‘starving’, with her hair a mess.
Finally, Wintour left Stone, who had disliked playing second fiddle to her career, for Shaffer. Her colleague Jordan Schaps was glad to see Wintour moving on from Stone. ‘I thought he put her down, and I didn’t like that,’ he says.
Strike a pose: Anna out with her friend Anne McNally in the 1990s
A South African by birth, Shaffer, who had been married before, was slightly hunchbacked and not handsome. He was also completely different from the playboy types Wintour had previously dated. Anna’s father Charles noticed that Anna had many boyfriends, and that she had a type, which he described as ‘unusually appealing but highly unstable’ characters.
Wintour, now in her early 30s, knew she wanted children. In Shaffer, she may have seen that future. For her, the relationship provided not only adoration but fortification. Shaffer, an intellectual who took her and her work as seriously as she did, put her on a pedestal.
Being the fashion girl in both the newsroom and within her family had left her feeling like she always had to prove herself. With Shaffer, she didn’t have to worry about that.
Although self-conscious about how he looked compared to her, Shaffer seemed just as dedicated to her professional success as she was. It was their alliance that spun Wintour’s talent and already unwavering determination into pure force.
But some friends saw something sinister in his support of Wintour. Perhaps stemming from his psychiatric training, he seemed to enjoy pitting people against one another, playing mind games as only a professional could. Two of their friends independently described Shaffer, who would phone her at her office multiple times a day, as Wintour’s ‘Svengali’.
In the evenings, she would show Vogue articles and page proofs to Shaffer. ‘He read things, and there were times that she would come back with a manuscript and there were words that were not in her vocabulary that she used to discuss the article,’ remembered former colleague Laurie Jones. ‘And then, if you wanted to question it, she shut you down.’
According to another former colleague, Andre Leon Talley: ‘We all knew that Dr Shaffer was the shadow editor of Vogue. The book [a mock-up of the magazine made up of page proofs] went home with her every night. So, of course, she’s going to discuss that with her husband.’
British-American editor & journalist Anna Wintour and British Pediatric Psychiatrist Dr David Shaffer attend the 95th Season of the New York City Ballet Party in 1991
The couple had married in September 1984 at Wintour’s Manhattan townhouse. A few days beforehand she had been contacted by record producer Michel Esteban, a former boyfriend, who said he was in New York and invited her for lunch or a drink. He was one of the exes, family members and just two Vogue colleagues who watched Wintour’s father walk her down the stairs of her house to the ground floor where the low-key, unfussy wedding was held.
Writer Joan Juliet Buck, later to become editor of French Vogue, was her only attendant. Despite living her life in the spotlight, Wintour has never cared to be the centre of attention.
Three years into Wintour’s editorship of Vogue, she rented a house in France where she entertained family members including her father and stepmother, her sister Nora and her husband and daughter, and her brother Patrick and his partner.
Shaffer’s two sons from his first marriage were also present for part of the time. Housekeepers came nearly every day. ‘I am still amazed at her lifestyle,’ her father remarked.
By then, Shaffer and Wintour had their own children, Charles, born in 1985, and Katherine, known as Bee, born in 1987. Wintour seemed to come alive when she talked about her young children, remembers former Vogue copywriter Lesley Jane Seymour. ‘She became much warmer — much less the fashion icon that you are terrified of.’
Wintour fitted in time with her children around her job, taking them to school each day in her chauffeur-driven car at 7.15am. In a 1998 interview, she called herself ‘religious’ about not staying late at work so she could go home and have dinner with them. And she said she ‘[tried] not to go out more than two or three nights a week’ or at weekends.
Whatever she was doing at work, if her children ever called, she answered the phone, say colleagues. And she attended events whenever she could.
Fellow parents remember gathering in her kitchen for a Halloween party for Charlie’s friends one autumn.
One of Wintour’s stepsons came over, and she made him a pot of coffee and unloaded the dishwasher while she chatted to the other parents.
‘She’s a busy woman, but she showed up and did her level best as a mom,’ recalls Susan Bidel, who was there that evening. ‘Our sons had play-dates. She invited kids for sleep-overs. She went the whole nine yards as an active mom, as much as her job would allow.’
Like Wintour’s own early days, her children spent a lot of time with nannies. One, Lori Feldt, who lived with the family in 1997, said it was her responsibility to get the children ready for school each morning, at which point they would see Wintour and Shaffer.
Anna Wintour and ex-husband David Schaffer who she married in 1984 and divorced in 1999
Contradicting what Wintour had said, Feldt remarked that the children often wouldn’t see their parents again until the next morning as they went to so many events at night. Feldt didn’t see much of the couple either, mostly communicating by writing messages in a notebook left in the kitchen, to which she would receive printed, typed replies. Wintour and Shaffer also used her as a personal assistant and household manager — one of an army of people who have performed such roles over the years.
In a system which ran throughout much of the past decade, Wintour regularly had two or three assistants working for her at any one time, all with highly ritualised jobs.
The first assistant managed the other two, handled Wintour’s schedule and was the primary point of communication.
The second liaised with the caretakers and chef at Wintour’s homes in Manhattan and Long Island, coordinated film screenings and took care of her three dogs, all named after characters in the novel To Kill A Mockingbird.
After one of the animals went missing, all three pets were fitted with tracking devices, for which the second assistant was responsible.
The third assistant ran errands, picked up theatre tickets and ordered Wintour’s clothes directly from designers, generally a customised catwalk look.
‘Usually someone in her office sends an email and says, “Anna loved this and this and this and this,” ’ said designer Tom Ford, one of her closest friends. A garment is then made in her size and sent over. The second and third assistants alternated being on call at weekends.
Designer Karl Lagerfeld and Editor-in-Chief of Vogue, Anna Wintour visit Macy’s Herald Square in New York City in 2006
Wintour sent all three assistants constant emails, asking for things: ‘Get me on the phone with this person.’ ‘I need to see that person.’ ‘Coffee please.’
And all three would be at the Vogue office between 7am and 7.30am to prepare for Wintour’s arrival. They pulled up a blank Word document or email draft to furiously type everything she said once she walked in. As soon as she arrived, she just started talking, issuing to-dos without pauses.
Meredith Asplundh started as an intern at Conde Nast in 1993, and a month into the job was hired to be Wintour’s second assistant. Before Wintour arrived each morning, she called the office from her car to warn the assistants of her approach.
‘I’m 15 minutes away,’ she’d say, which was Asplundh’s cue to go downstairs to get her whole-milk latte, praying the lift wouldn’t be slow because if the coffee wasn’t there when she arrived, Wintour would seem ‘testy’. Asplundh understood — she would also be annoyed if her coffee was late.
Appearance was as important for the assistants as for the rest of the staff. Asplundh didn’t have the money to buy an all-designer wardrobe, but her fashion-conscious mother gave her hand-me-downs. Wintour generally approved.
Still, Asplundh said, there were times when ‘she would glare at whatever I was wearing. It wasn’t a glare like approval. It was sort of, What the hell is that? You could definitely tell when she was like, “Why would you put those pants with that top?” ’
But the hardest part of the job was handling the requests from Wintour that were delivered with almost no background information. Many of these directives came with the tacit understanding — or explicit instruction from the first assistant — that you could not ask Wintour for clarification or help. Assistants were afraid even to ask her what she had written on a piece of paper.
Not everyone endured. Days could easily last 12 hours or more, and assistants woke up in the middle of the night thinking about Wintour and feeling they ought to check their email and do things for her. But despite the difficulty and stress, the young women who lasted did so because they respected Wintour and saw working for her as a huge opportunity.
Anna Wintour and David Schaffer during a book party for ‘Holy Terror: Andy Warhol Close Up at The Factory in New York
Some also saw criticism of her controlling nature as something that men with power don’t have to endure — a view shared by many others on her staff.
As a young fashion assistant in London in the 1970s, Wintour got daily calls from men wanting to take her out, an early assistant remembered, among them the actor Terence Stamp.
Her circle from that era included the Daily Mail’s gossip columnist Nigel Dempster, nearly a decade older than her, whom she dated (though she later denied it), and his journalist friends Anthony Haden-Guest and Jon Bradshaw, with whom she began a five-year relationship when she was 23.
Bradshaw was swashbuckling, drank a lot and loved to gamble. Twelve years older than Wintour, the New Yorker had moved to London from the U.S. and was writing for Harpers & Queen while she was working there.
‘There just weren’t many people like Bradshaw,’ she said. ‘He stood out. He would walk into a room and own that room. The polar opposite of the upper-class English world that I knew when I was growing up. He was not so polite and not so careful, wore jeans, had that great smile, and was just much more open. And yeah, a little bit dangerous.’
In the spring of 1976, after they had moved to New York together, Bradshaw took her to see one of reggae superstar Bob Marley’s four sold-out shows. The next morning, Wintour told colleagues: ‘I feel like I’ve met God.’
This story got misconstrued into reports that Wintour disappeared for two weeks to have an affair with Marley. She later called the rumours ‘fake news’ and said she never met him. Another person Wintour dated at around this time was the journalist Christopher Hitchens, whom she said she was ‘mad about’.
Many of the men she has had relationships with were older, and many were writers. Above all, she seemed attracted to people with life experience, intellect, and ambition. Shelby Bryan was no exception. Wintour had been married for around ten years when she met Bryan, then the CEO of ICG, a fibre-optic networking business, at a fundraising ball with his wife, Katherine. By 1999, his company had annual revenues of $500 million (£312 million), with a projected $1 billion (£670 million) in 2000. He was the first boyfriend Anna had with that kind of wealth.
Anna pictured with longtime lover Shelby Bryan at the Evening Standard Drama Awards in 2000
Bryan had been to so many such parties that little struck him about the evening except for Wintour, whom he found both attractive and brilliant. He had only a vague sense of who she was at that point and was intrigued enough to call her and invite her to lunch. ‘I think that we both were fond of each other over a relatively short period of time,’ Bryan said.
Neither hid that they were married, and an affair unfolded.
It wasn’t as if Wintour had seemed miserable with her husband, David Shaffer. Toward the end of the 1990s, they appeared to have a smooth domestic life. But Wintour was reportedly bored by their marriage — as she became dazzled by Bryan, who had money, impeccable connections and good looks.
However, looks didn’t seem to be what Wintour primarily admired in men, some observed. After a lunch with Bill Gates, when Microsoft was on the rise, she came back to the office and told a colleague, Laurie Jones, how attractive she thought he was. Jones just thought, God, she’s attracted to people who are powerful.
Unlike Shaffer, whom friends called ‘complicated,’ Bryan was straightforward. Though Wintour agonised over how a divorce would affect her children, she initiated proceedings in September 1999.
Anna Wintour with Shelby Bryan arriving at the New Yorkers for Children Fall Gala at the Regent Wall Street in New York City. September 17, 2002.
She knew from her own father how painful having a cheating parent was, yet here she was inflicting that same pain on her children.
Some close to Wintour were surprised she ended up with Bryan. He was smart and cultured — he would steal away from boring lunch conversations to listen to Wagner CDs — but Vogue staff who interacted with him at parties said he could be crass and seemed to lack Wintour’s self-control.
He was the kind of man, some felt, with a sense of humour straight off the trading floor of the stock exchange in the 1980s. Three people with knowledge of his behaviour said he joked freely about things like how good he was ‘in the sack’, and ‘grabbed women’s butts’.
‘I’ve never done that,’ Bryan said, denying any inappropriate behaviour. To Laurie Jones, some of his behaviour toward Wintour ‘was just not kind’.
Designer Tom Ford met Bryan at the home of a mutual friend in England around five years into the relationship.
‘To me, he was very familiar because he was like very many Texas men who I grew up with. He says what he thinks. He’s not afraid of saying things that other people might be shocked at. He can be very off-the-cuff, and kind of in that way, the opposite of Anna. When I realised, wow, this is who she has chosen to be with and he’s kind of wild, I thought, wow, OK. This is a totally different side here I didn’t know.’
Wintour’s new relationship was different from her marriage. She and Bryan never married and never moved in together. Once it became public and they had separated from their spouses, they settled into a rhythm of seeing each other mostly at weekends because they were so busy during the week.
Wintour would read drafts of Vogue articles, but she almost never asked Bryan’s opinion. The relationship didn’t last and in 2020 news broke that the couple had parted.
FOR many, Wintour has been a source of admiration and envy. Yet it is probably her fearsome professional reputation that first comes to mind when her name is mentioned.
David Shaffer, at around the time of their divorce, told friend Anthony Haden-Guest: ‘Anna has no empathy.’ But others thought that she did possess empathy — it just seemed as if she sometimes left it at home, strictly reserved for certain aspects of her personal life. Many are agreed that outside the office she is different.
Anna Wintour daughter Bee Shaffer and son Charlie Shaffer during The Zac Posen Spring 2008 Collection, held in Bryant Park, New York
At her weekend compound on Long Island, say friends, she’s relaxed and loves to host her extended family. ‘She’s become a matriarch,’ says her old friend Emma Soames. ‘She’s very family-minded.’
As her long-time Met Gala planner Stephanie Winston Wolkoff puts it: ‘There is a person there.’
Wintour likes to start her weekends on Long Island by putting on a Prada tracksuit for an 8am game of tennis. ‘She just never misses shots,’ said friend Miranda Brooks.
Lunches and dinners for around 30 guests are often followed by games. After dinner, visitors might move to one of the barns on her property where a disco ball spins.
Everyone drinks and dances, including Wintour, until she slips away before everyone else.
Each summer she holds a camp for her closest friends and family. They can take art classes, swim, sing or play tennis with her instructor (or even with Roger Federer, who came one year for her birthday).
Anna pictured with long-term companion and mobile phone millionaire, Texan Shelby Bryan in 2007
‘She has a whole tennis camp and there are trophies and everything like that. It’s usually a family member [who] wins. But it’s very highly competitive,’ said her friend and colleague Lisa Love.
She also holds ‘movie nights and casino nights and theme events constantly. She likes to party’.
Both Wintour’s children got married on Long Island — Charlie in 2014 to his college sweetheart, and Bee in 2018, in a ceremony conducted by actor Colin Firth, to the son of beloved Italian Vogue editor Franca Sozzani.
In a major milestone, Wintour became a grandmother in 2017.
‘She loves the grandchildren,’ said her old friend Anne McNally, who saw Wintour play with the baby girl and change her nappies.
A second granddaughter followed in 2019. It’s not as if the children know their grandmother is the Anna Wintour.
There is plenty of time for that. But of course, even while babysitting, said McNally, ‘she is still Anna’.
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 (offer valid to May 14, 2022; UK P&P free on orders over £20), visit www.mailshop.co.uk/books or call 020 3176 2937.