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'Fascinating' Sunday Times 'Deeply sourced and rich with anecdotes' The Times 'Like a nonfiction version of TheDevil Wears Prada' Elizabeth Day 'Odell's extensive reporting dredges up a wealth of delightful details' New York Times This definitive biography of Anna Wintour chronicles the steep climb of an ambitious young woman who would, with singular and legendary focus, become the most powerful woman in media. As a child, Anna Wintour was a tomboy with no apparent interest in clothing but, seduced by the miniskirts and bob haircuts of swinging 1960s London, she grew into a fashion-obsessed teenager. Her father, the influential editor of the Evening Standard, loomed large in her life, and once he decided she should become editor in chief of Vogue, she never looked back. Impatient to start her career, she left high school and got a job at a fashionable boutique in London - an experience that would be the first of many defeats. Undeterred, she found work in the competitive world of magazines, eventually moving to New York. Before long, Anna's journey to Vogue became a battle to ascend, no matter who or what stood in her way. Once she was crowned editor in chief - in one of the stormiest transitions in fashion magazine history - she continued the fight to retain her enviable position, ultimately rising to dominate all of Condé Nast. Based on extensive interviews with Anna Wintour's closest friends and collaborators, including some of the biggest names in fashion, journalist Amy Odell has crafted the most revealing portrait of Wintour ever published. Weaving Anna's personal story into a larger narrative about the hierarchical dynamics of the fashion industry and the complex world of Condé Nast, Anna charts the relentless ambition of the woman who would become an icon.
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ANNA
‘An impressively detailed portrait that reveals much about Wintour’s management style and early career’ Financial Times, Books of the Year
‘Odell’s book is deeply sourced and rich with anecdotes. Although she’s clearly sympathetic to her subject, she’s direct in addressing Wintour’s missteps’ The Times
‘Odell’s extensive reporting dredges up a wealth of delightful details...You’ll walk away knowing every step – and misstep – in Wintour’s famous ascent to the heights of magazinedom’ New York Times
‘The secret to [Anna’s] longevity is the subject of Odell’s biography, which is drawn from interviews with Wintour’s tightknit inner circle. Given that she’s famously private and notoriously aloof, the participation of intimates in the book’s reporting indicates a green light from Wintour herself. But Odell is unsparing, detailing Wintour’s ambitious rise and ruthless power grabs, dotting the narrative with a healthy amount of gossip and color’ Bloomberg Businessweek
‘A dissection of one of fashion’s most controversial figures and a window into the glossy pages of Vogue, Amy Odell’s definitive Anna Wintour bio balances criticism with understanding and stories of true sadism: Imagine telling Oprah to lose 20 pounds for a cover’ Rolling Stone
‘A fascinating portrait of the secretive queen of fashion. The devil is in the detail’ Andrew Morton
‘Odell takes her readers behind Wintour’s iconic bob and sunglasses in this deeply researched account, delivering a close-up view of the most powerful woman in fashion’ Sara Gay Forden, author of The House of Gucci
‘Amy Odell’s new book is a wonderful romp through Wintour’s world: couture at its juiciest. But it is more than that: an intimate guide to how the queen of fashion built and manages her magic kingdom’ Washington Post
‘[A] stunningly thorough, balanced, humanizing portrait of the most powerful woman working in fashion, and one of the most powerful business leaders in America…. After speaking with over 250 sources and poring over letters and magazines, Odell gives us countless juicier, more illuminating details to gobble up’ The Cut
‘A highly detailed and revelatory portrait of a very private figure’ CNN.com
‘Anna: The Biography pulls off a rare feat. It’s a comprehensive and balanced look at Wintour’s long, storied, and often controversial career, but it’s also a great read’ Texas Monthly
‘Having interviewed over 250 sources (many of whom are unforgettable and quotable characters themselves)…Odell takes readers through Wintour’s lifelong love of fashion, her personal life and romantic relationships, and, primarily, her decades-long career... While Odell’s nimble writing moves at a clip, the extent and detail here make this perfect for fashion devotees and fans of publishing industry tales as Anna’s career coincides with sea changes in magazine journalism’ Booklist (starred review)
‘What scintillates…are the intimate details about a famously inscrutable subject…as well as the blunt treatment of Wintour’s more problematic sides….[a] fascinating look at an enigmatic figure’ Publishers Weekly
‘The most comprehensive biography of the media icon…[Anna] fascinates with Odell’s well-documented account of Wintour’s broad influence’ Library Journal
‘The details of Anna Wintour’s life have been kept as tantalizingly hidden as her eyes behind her trademark sunglasses. This book tells her stunning story. Extraordinarily sweeping, astute, and unputdownable’ Sheila Weller, New York Times bestselling author of Carrie Fisher: A Life on the Edge
‘Anna is brilliantly written and well-researched, full of the kinds of details you›ve always wanted to know about Wintour›s early life, and the ways in which she used her considerable gifts to amass astonishing, and enduring, power and influence’ Laurie Woolever, author of Bourdain, The Definitive Oral Biography
ALSO BY AMY ODELL
Tales from the Back Row
The Biography
Amy Odell
First published in Great Britain in 2022 by Allen & Unwin First published in the United States in 2022 by Gallery Books, an imprint of Simon & Schuster, Inc.
Copyright © 2022 by Amy Odell
The moral right of Amy Odell to be identified as the author of this work has been asserted by her in accordance with the Copyright, Designs and Patents Act of 1988.
All rights reserved. No part of this book may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, recording or by any information storage and retrieval system, without prior permission in writing from the publisher.
Every effort has been made to trace or contact all copyright holders. The publishers will be pleased to make good any omissions or rectify any mistakes brought to their attention at the earliest opportunity.
Allen & Unwin
c/o Atlantic Books
Ormond House
26–27 Boswell Street
London WC1N 3JZ
Phone: 020 7269 1610
Email: [email protected]
Web: www.allenandunwin.com/uk
A CIP catalogue record for this book is available from the British Library.
Interior design by Jaime Putorti
Hardback ISBN 978 1 83895 725 4
Trade paperback ISBN 978 1 83895 726 1
E-book ISBN 978 1 83895 727 8
Printed in
10 9 8 7 6 5 4 3 2 1
For Rick
Introduction
1 Origins
2 Beyond School Uniforms
3 Fired and Hired
4 Anna Wintour, Fashion Assistant
5 A New Start in New York City
6 Viva la Vida
7 A Savvy Move
8 In Vogue
9 Second Best
10 A Tale of Two Vogues
11 House & Garment
12 Anna Wintour, Editor-in-Chief
13 Calculated Risk
14 “In” versus “Out”
15 First Assistant, Second Assistant
16 A New Project, an Old Friend
17 Follow the Money
18 The Divorce
19 Dot.Com
20 A New Alliance
21 Mutual Benefit
22 Big Vogue
23 The Crash
24 Politics and Pain
25 Anna Wintour, Artistic Director
26 Changes
27 The Met Gala
Epilogue: The Pandemic
Author’s Note
Acknowledgments
Notes
Index
About the Author
“People tend to cast people in clichés.”
—Anna Wintour,
New York, October 18, 2018
ANNA
Of course, she was wearing the sunglasses.
Anna Wintour walked into the Vogue staff meeting and looked at the group that had gathered around the table about ten thirty that morning. Many of them had been working late into the night, coming up with stories attempting to explain the unprecedented. Others had just been up crying, scared, in shock. Anna had extraordinary influence over a great many things, but the outcome of this election was not one of them.
It was November 9, 2016. Despite Hillary Clinton’s loss, after Vogue’s full-throttle support, including an endorsement—the first of its kind in the magazine’s 124-year history—Anna started the day as usual. She rose by 5:00 a.m., exercised at 5:30 or 6:00 (depending on whether she played her twice weekly tennis or worked out with her trainer), sat for thirty minutes for professional hair and makeup, and was then chauffeured to her office at 1 World Trade Center, where her three assistants and her usual breakfast—a whole-milk latte and a blueberry muffin from Starbucks, which would mostly go uneaten—were waiting for her.
When she arrived that morning, wearing tall python boots and a printed red dress, Anna told the first assistant to call an all-staff meeting. Her requests for her assistants were constant—day and night, weekday and weekend, and always delivered in emails with no subject line. Her schedule was meticulously planned, but this meeting was last-minute, and she asked her assistants to attend, which was unusual. No one knew the purpose of the gathering, but they did know that when Anna called for one, if you didn’t arrive early, you were late.
Phillip Picardi, the editorial director of Teen Vogue’s website, had originally given his team permission to work from home that day. Covering the election live for the first time in the magazine’s history, they had all worked late trying to explain Donald Trump’s victory to the millions of teenage girls who had expected proof that they too could become anything, the same way Anna had.
At seven thirty that morning, only three hours after Picardi had finally called it a night, his assistant had reached out about Anna’s all-hands meeting. He’d called his exhausted, emotionally spent staff, and told them to get to the office.
Seats at the white conference room table filled up, and staff packed into every remaining space behind them, waiting for Anna. The polish associated with Vogue employees is legendary, but that morning everyone—except Anna—looked some version of terrible, Picardi recalled.
One of Anna’s biggest strengths as a businessperson and a leader has been letting nothing slow her down or stand in her way—not childbirth, not emotion, not corporate bullshit, and not losing—and she had correctly sensed that her team needed a filament of the same hardy fiber at this particular moment.
“There’s an article that came out today accusing me of going too far in supporting Hillary Clinton, the first woman to ever win the Democratic presidential bid for president,” she said, standing at the front of the room. She was referring to a piece published that morning in the fashion industry newspaper Women’s Wear Daily (commonly referred to as WWD), with the headline “Did Anna Wintour and Vogue’s Hillary Clinton Advocacy Go Too Far?”
“With the bitter election now in the rearview mirror, many questions loom for Vogue, women’s magazines, and the fashion industry,” the article went on. “To name a few: Did Vogue lose credibility with its readers? Should women’s magazines cover stories like news outlets? Did Anna go too far in her role as editor?”
Anna was believed to have been angling for an ambassadorship, which would have brought an end to her reign at Vogue. While Clinton thought Anna would have been a great ambassador, and nominating her was a possibility, she hadn’t begun a formal process for filling those positions, an advisor said. It was unclear to both the campaign and Anna’s boss that she had serious interest in it. Her then-boyfriend, Shelby Bryan, said, “If she’d been offered the ambassadorship to the UK, I think she would have had to really think hard about that.”
Surveying her staff in the conference room, Anna continued, “I would just like to say to everyone gathered here today, who works for me, that if supporting LGBTQ rights, if supporting women’s rights, if supporting women running for office, if supporting immigrants, and if supporting people all over the country for equality means going too far, then I hope all of you go too far every single day.”
As she spoke, her voice caught. It was something that happened rarely, and noticeable enough that a former employee, Stephanie Winston Wolkoff, had a name for it: “the crackle.” The Vogue team knew she had to have been hurt by Clinton’s loss, but they’d never expected confirmation from Anna herself, a woman who almost never showed her emotions at work and, in fact, was so averse to doing so that she’d habitually placed sunglasses between any hint of sentiment and the rest of the world for most of her life. She once described them in a CNN interview as “incredibly useful” for when she wants to hide what she’s really thinking or feeling—“a crutch.” But at this moment, the shield slipped and she did something that she hadn’t the night before.
She was crying.
Anna’s way had always been to move forward rather than dwell on what could have been, and that pattern held. “But he’s the president,” Anna said. “We have to figure out a way to keep moving forward.”
Her statement made, she departed. The staff applauded, and then texted anyone who, for whatever reason—a photo shoot, travel, the usual business of the day—was out of the office: “Oh my god—Anna just cried in front of everyone.”
* * *
Before Trump was inaugurated and while her staff were still trying to process their feelings about his win, Anna begrudgingly reached out. Trump had been a welcome guest at many of her events in the past, seemingly as interested in her influence and approval as she was in his checkbook. She arranged to meet with him at Trump Tower, through his daughter Ivanka, a longtime acquaintance. Donald told his wife Melania that Anna was coming to see him. According to Melania’s then-friend Stephanie Winston Wolkoff, she had heard nothing from Anna herself about the visit, and was so offended she didn’t even say hello when Anna showed up. Melania didn’t understand that she had been invited to Anna’s events not because she was a friend, but simply because she had appeared on the February 2005 cover of Vogue.
Anna arranged to bring Donald to 1 World Trade Center to sit down with Condé Nast’s other editors-in-chief. As those around her well knew, while Anna’s motives weren’t always clear in the moment, there was always an agenda. Who wouldn’t want an audience with the president-elect? people in the meeting with Trump supposed she reasoned. Her team tried twice, once before Trump’s inauguration and once after, to photograph Melania for Vogue. But in part since they wouldn’t guarantee a cover, Melania wouldn’t do it. “I don’t give a fuck about Vogue or any other magazine,” she said.
But, Winston Wolkoff believed, she did give a fuck about Vogue. She wanted the cover once more.
Anna Wintour has been the editor-in-chief of Vogue since 1988, and one of the most powerful figures in media. “I don’t know what it is about Anna exactly,” said Laurie Schechter, an early assistant, “but if she could bottle it she’d make a million billion dollars because it just was like fairy-tale stuff.” Yet the many people interviewed for this book had a hard time explaining why she is so powerful and what her power amounts to.
Across more than three decades’ worth of issues of Vogue and its spinoffs, she has defined not only fashion trends but also beauty standards, telling millions of people what to buy, how to look, and who to care about. She decides which celebrities and models to photograph and which clothes to dress them in. If she wants a designer to have more influence, she recommends them to lead bigger labels, and she has this power because the owners of those larger labels seek—and follow—her advice. Said Grace Coddington, Anna’s former creative director, about the power of her preferences: “She makes it very clear. So obviously it’s not a good idea to continue in a track that you know she doesn’t like, because then she’s probably not going to like the pictures, and if she doesn’t like the pictures, they might run, but there’d be many less.”
“I haven’t ever heard her say, ‘Do not do that, do this.’ You know somebody loves something by looking at them, and you know if somebody is indifferent by looking at them,” said Tonne Goodman, a fashion editor who’s worked for Anna since 1999 and attended many collection previews with her. Sally Singer, who worked for Anna for nearly twenty years, elaborated, “There was never an idea that Vogue was an editorial project alone. It was an intervention into the fashion world.”
That intervention has been largely successful, given the effect of her authority. Tom Ford, a giant in the fashion industry and one of Anna’s closest friends, has long enjoyed the distinction of being a “Vogue brand.” Such favorites have privileged relationships with Anna and her team of editors; she and her staff advise them not only on their clothes, but also on how to run their businesses. In turn, Vogue brands are rewarded with coverage in the magazine and, more important, Anna’s personal support and advice. And she doesn’t wait for the next generation of designers to emerge—she financially supports them, through the Council of Fashion Designers of America (CFDA)/Vogue Fashion Fund. That support can be the difference between unimaginable success and bankruptcy. “If I were on her good side, I would be afraid,” said André Leon Talley, once one of Anna’s closest collaborators, about the danger of falling out of favor. “As much as she loves a person who has talent, if she does not love you, then you’re in trouble.”
This kind of interventionist strategy isn’t limited to the fashion world. She has leveraged the names of her powerful allies to raise money for charitable initiatives, most notably the Metropolitan Museum of Art’s Costume Institute, which preserves and displays objects of fashion as art, for which she has amassed more than $250 million. She has organized the fashion industry’s efforts to raise money for Democratic candidates, thereby visibly politicizing the business. Her influence extends to Broadway, entertainment, and sports, among other areas. (First-time director Bradley Cooper, who repeatedly sought her advice, sent her a copy of his script for A Star Is Born to get her thoughts on whom to cast in the lead role, which went to Lady Gaga.)
Editors of Vogue were powerful before Anna had the job, but she has expanded that power remarkably, making the magazine, and herself, a brand that powerful people want to be associated with. “The amazing thing about Anna is the average person knows who she is,” said Ford. “You show them a picture and they say, ‘That’s Anna Wintour from Vogue.’” Particularly thanks to the novel and film The Devil Wears Prada, how Anna speaks, hires and fires, eats, and shops are topics of both obsession and scrutiny. She is widely perceived as “cold” and “icy,” endowed with the rare ability to turn attachments—to both outcomes and people—on and off like a switch. When she walks the halls at Condé Nast, terrified staff press themselves against the wall to stay out of her way and check what’s on their computer screens. Yet they are devoted to her—indeed, many former staffers feel the need to protect Anna because working for her was as extraordinary as it was grueling. Certainly she doesn’t make it easy for them. Staff responsibilities go beyond running Vogue, said Mark Holgate, who joined as senior fashion writer at the end of 2003. “It’s also, ‘Come up with a list of designers for someone to consider hiring as their new creative director.’ It’s, ‘Can you look at this script because so-and-so’s come to Anna with an idea. . . .’ There’s a ton of other things funneling into Vogue on any given day.” And when Anna asks for something, she usually wants it done immediately. Despite her work emails to her staff going out before 6 a.m. some days, added Holgate, “It’s also kind of addictive.” Others praise her directness; you always know where you stand with her, and that’s better than working for someone who wants to know about your kid’s birthday party but can’t make up their mind about a headline.
Those who have worked for Anna often wonder why she has to be involved in everything, and how she manages to juggle it all. Anna controls all that she can, right down to the ingredients in the food at the Met Gala. Yet despite her perfectionism, she has made her fair share of mistakes. For someone who has espoused progressive principles like those she mentioned in the postelection staff meeting, her track record is spotty. She has been repeatedly called out for publishing culturally and racially insensitive photos and articles, and for failing to embrace diverse subjects. Years went by in the nineties when only white women appeared on the cover of Vogue. Promoting fur was once her cause célèbre. She has publicly body-shamed. Her staff has been mostly white, seemingly picked for their personal style, appearance, and pedigree as much as for their skills and credentials.
For many, Anna has been a source of admiration and envy. (As one of her old friends, Annabel Hodin, concluded, “All you ever wanted to do was to be her, really.”) Yet it is probably her fearsome reputation that first comes to mind when her name is mentioned. With so few women having attained Anna’s level, there’s no model for how that should look, just the feeling that such power should be exercised with a warmer touch than she naturally possesses. (Though if a man did her job as well and with similar affectations, his discipline and commitment would likely be celebrated.)
Outside of the office, Anna is said to be different. She is a dog person. She is, friends said, fiercely devoted to her children and grandchildren (yes, she’s changed their diapers). At her weekend compound in Mastic on Long Island, they added, she’s relaxed. She loves hosting her extended family and serving meals to as many as fifty people. “She’s very family-minded,” said Emma Soames, a longtime friend. “She’s become a matriarch.” As her longtime Met Gala planner Stephanie Winston Wolkoff put it, “There is a person there.”
Inside the office, some staff view her similarly. Jill Demling, who booked celebrity covers for Vogue for twenty years, stated, “Anna played an important role in my life, not only as a mentor, but as almost a mother figure.” Yet she remains full of contradiction. Anna doesn’t do small talk. Yet she enjoys people who aren’t afraid to pop into her office and ask her a question. She is deadly serious about business, yet she likes to joke around with her staff. What she really wants, what she responds better to than anything, is being treated like a human being. Like those famous sunglasses, her icon status has been both an ennobling veneer and an obstacle.
There is debate about how creative Anna is as an editor. Some who have worked closely with her think her strengths are actually twofold: first, managing creative people and the creative process, and second, forming politically savvy alliances to grow her power. Her closest friends said that she absolutely loves fashion, though that wasn’t always evident to others who worked closely with her. They wondered if fashion was just her way, as a woman entering the workforce in the era that she did, to attain a position of real power.
Over the course of her reign at Vogue, her resignation or dismissal has been a subject of regular speculation. But, despite spates of acute public criticism, her power only expands with time, because she knows the ecosystem in which she operates better than anyone. You might even say she invented it.
Born Eleanor Baker to a wealthy Quaker family in 1917 in Harrisburg, Pennsylvania, the future Nonie Wintour was a society girl. Her father, Ralph Baker, was a lawyer who left private practice to become a Harvard Law School professor. He specialized in trusts, and, before his death, established a substantial fund that would support his descendants, including his granddaughter Anna, over the course of many decades.
Nonie had enrolled at the University of Cambridge’s Newnham College for women after graduating from Radcliffe in 1938, and was introduced to her future husband, Charles Wintour, also at Cambridge, by their mutual friend Arthur M. Schlesinger, Jr. The son of a major general, Charles was born in 1917 in Dorset in Southwest England. Petite and slim, Nonie styled her hair in short dark waves pinned back from her face. Charles wore glasses and a melancholic expression, and projected an air of professionalism.
Both shared an interest in journalism and writing. At Cambridge, Charles co-edited Granta, the prestigious undergraduate literary magazine. Nonie had spent the summer after college working as a reporter at the Daily Republican newspaper in Phoenixville, Pennsylvania. The necessary terseness of newspaper journalism might have encouraged her direct and spare use of language, which sometimes drove Charles crazy when they were dating, since he often couldn’t tell, particularly in their correspondence, what she was actually thinking.
After graduating with a first for academic achievement, the university’s highest possible honor, Charles headed to London to start working at the J. Walter Thompson advertising agency, while Nonie headed back across the ocean—their love was certain, their future anything but.
Among the most minor consequences of Germany’s invasion of Poland on September 1, 1939, was Charles being out of a job at J. Walter Thompson barely two months after he’d arrived. Like so many of his peers, Charles promptly enlisted. Before he knew what his assignment would be, he sent a letter to Nonie asking her to come to London and marry him as soon as possible. Weeks later he began officer cadet training, and shortly afterward received word that Nonie accepted and would come in February.
Nonie arrived on the same day the first enemy aircraft was shot down in the UK. Charles was so ecstatic to see her that he nearly fainted. While a bit less euphoric, Nonie was relieved that they still got along so well.
They married on February 13, 1940, at a church in Cambridge, and then celebrated with friends. As thrilled as they were to be together, the war was disheartening and neither of them knew where Charles would be sent now. Soon pregnant, Nonie stayed on a few months before returning to Boston.
Once alone, Charles slid into depression. Terrified of an invasion of Britain, he wondered if an affair might be the antidote. This was only half as shocking as it seemed. Charles felt that being with a woman was a “necessity” for him, and from their earliest weeks together, Nonie had realized that he wasn’t the faithful type. Feeling that a ground rule had been established and accepted, he assumed Nonie would agree that an extramarital relationship would benefit him. (Charles’s affairs would go on throughout their marriage, becoming painfully apparent to Anna as a teenager.) Nonie—then about six months pregnant—consented to the affair from Boston. Though he worried whether it actually bothered her, Charles started spending his evenings with a twenty-three-year-old divorcée whose new fiancé was conveniently in Rhodesia.
In late November, forty weeks and a day after his wedding, Charles received a cable from Schlesinger announcing the birth of his son Gerald, named for Charles’s father. Half a decade would pass before he would meet his son.
For Anna, one of the most difficult periods of her personal and professional life would involve living with a new baby on the other side of the ocean from her spouse. Her parents had to manage this very challenge in the middle of a war, with intense worry that Charles could be killed any day.
Just months after having Gerald, Nonie—after Charles fought with her father about it—sailed back to Europe to be with her husband, leaving their son in safety with her parents. Charles was aware that Nonie came against her will. He had pressured her to come, though she felt deep pain at leaving Gerald behind. Still, Charles was aware that no available course of action would leave either of them entirely happy, and that if they didn’t see one another until after the war, their youth would have fled them—that is, if he even lived through the war itself.
While initially homesick and angry, Nonie stayed with Charles for several years, choosing to be present in her marriage, even if that meant estrangement from her child. She moved through the UK following wherever Charles’s various posts took him as he ascended in the ranks, both of them grateful when he was assigned to office work after completing a course at the Staff College. She finally sailed home in the middle of 1944, now a stranger to their son. With his wife on the other side of the Atlantic, Charles began another affair. Nonie had left her baby for her husband for several years. Now Charles was willing to abandon his wife through infidelity. Though the circumstances of war were exceptional, Charles and Nonie seemed to share an ability to disregard others’ welfare when it might get in the way of their most immediate desires.
In the winter, he was stationed in the Trianon Palace Hotel at Versailles, resplendent with crystal chandeliers, black-and-white-tiled floors, and white columns. Sitting in a garret, Charles and his fellow junior officers discussed what they wanted to do after the war. Charles said he wanted to become a journalist. Arthur Granard, an aide to Air Chief Marshal Arthur Tedder, responded, “If you ever want an introduction to Lord Beaverbrook, let me know.”
Lord Beaverbook was a wealthy Canadian who became a millionaire at twenty-seven by merging cement companies before moving to London to pursue business opportunities along with political and cultural influence. He advised Winston Churchill during the war and published a portfolio of newspapers (which just after World War II had the largest combined circulation of any publisher in the world), including the Daily Express and the Evening Standard. Having failed to become prime minister, Beaverbrook used his papers to promote his friends, attack his enemies, and push for an isolationist Britain.
Once the war ended, Charles wrote Granard to ask about meeting Beaverbrook. To his surprise, Granard followed through on his promise and made an introduction.
Beaverbrook was a known eccentric, but Charles found him disarmingly warm when they met at his apartment on London’s upscale Park Lane on Monday, October 1, 1945. He asked Charles to write an article on the differences between British and American work styles, and after filing the story, Charles received an offer to work as an assistant editorial writer at the Evening Standard on a trial basis for £14 a week, a job that would change his life.
With his career seemingly sorted, Charles now had to settle. He had one final night out as a bachelor with his lover, then found a place to rent for his family in London’s Hampstead neighborhood. He had no idea how short-lived his and Nonie’s happiness would be.
Gerald was five years old when Nonie brought him to London in early 1946. Almost immediately, Charles felt Gerald would benefit from living with him, after being brought up “in a predominately feminine environment.”
Nonie and Charles had their second son, James (known as Jimmie), in May of 1947, and two years later Nonie was pregnant again. On November 3, 1949, Nonie gave birth to her first daughter, the little girl she’d hoped for when Jimmie was born, named Anna. Aside from the baby’s bout of whooping cough the following spring, the Wintour children flourished.
That was until Tuesday, July 3, 1951, four months before Anna’s second birthday. Gerald put on his uniform and headed off to school. Now ten years old, he had been riding his bike for years. Tragically, a car hit Gerald while he was riding home that day, fracturing his skull. He was taken to New End Hospital in Hampstead, but could not be saved. At 6 p.m., twenty minutes after he arrived, Gerald Wintour was pronounced dead.
The story that would endure in British journalism circles was that this personal calamity spurred Charles’s professional ascent. He had been bored and itching to leave the paper for a magazine job. Still, when notified during a meeting with Beaverbrook that Gerald had been in the accident, rather than rush home, he is said to have gone back into the meeting and carried on with work, making no mention of his son. That dedication in the face of one of life’s worst tragedies left an indelible impression on his boss.
Nonetheless, Charles shared Nonie’s profound grief, in her case so great that her doctor prescribed her medication to help get her through the worst days early on. Both parents tormented themselves with blame; making it worse, eight days after the accident the man who’d been behind the wheel was charged not with manslaughter, but only dangerous driving. Though he faced a maximum jail sentence of two years, after ultimately being convicted, he was ordered to pay a fine of just £10.
Later that month, the Wintours packed up and sailed to America on the Queen Elizabeth to visit Nonie’s family. Charles, the sort who never took his full vacation time, departed the States early to return to work, and it would not be until the fall that the family was reunited. The trip, of course, couldn’t change their suffering.
Though Anna was twenty months old at the time of Gerald’s death—too young to remember the event or grasp the tragedy of the loss—her family was haunted by it for many years to come. No pictures of her brother were displayed in the house, and at one point, Nonie’s anxiety was such that she put bars on the windows, fearing that somehow one of her remaining children might fall out.
While his spirit may have been shattered, in the new year Charles got a promotion to political editor of the Evening Standard. A profile of Beaverbrook in Newsweek that mentioned Charles’s elevation called him “brilliant.” Though Nonie was proud of her husband’s success, she seemed to resent that it resulted from devotion to Beaverbrook, which appeared at times greater than Charles’s dedication to her and their children. She especially loathed Beaverbrook’s conservative politics.
Charles and Nonie went on to have two more children after Anna, Patrick and Nora. Bored at home raising her four kids, all under the age of ten, Nonie picked up freelance gigs reviewing television shows, reading scripts for Columbia Pictures, and finally writing as a film critic. When she was ready to work full-time again, “she decided that she wanted to work in social issues,” Anna later said, and began a whole new career as a social worker helping pregnant teens find adoptive parents for their children, dedicating herself to this effort as much as Charles did the newspaper. “That was very important work to her and I think very inspiring to all of us,” Anna said. Though she spoke often in interviews about her father as an inspiration, she almost never, over the course of her entire career, discussed her mother, despite how close they were. She rarely discussed her mother even privately with her friends. Yet her character strongly resembled Nonie’s. Anna* may have been more extroverted than Nonie, but, like her mother, Anna was incredibly strong-willed and would adopt equally fierce political convictions.
Anna’s professional ambition and ruthlessness, on the other hand, seemed to stem specifically from her father, whose power within the Beaverbrook stable grew with every promotion—from political editor of the Evening Standard to assistant editor at the Sunday Express to deputy editor of the Evening Standard to managing editor at the Daily Express and then, in 1959, back, to his relief, to the more upmarket Evening Standard.
Being editor of the Evening Standard was more than prestigious—it seemed financially advantageous. The Wintours bought a large twostory house in the English countryside, and when she wasn’t riding horses or playing tennis, one of Anna’s favorite things to do there was curl up on the quintessentially English cabbage-rose chintz upholstery with a book (friends and colleagues later marveled at Anna’s voracious reading). The Wintours’ vacations, usually during the summer, were along the Mediterranean, likely in Spain or Italy.
Charles kept a strict professional schedule. He rose at 7 a.m. and got to his office at 8, where he was responsible for putting out at least five different editions of the paper each day. If news broke when he wasn’t at the office, he dropped what he was doing and dashed back to work, even if the family was out of the country on vacation. “The family all knew that he cared very deeply about us, but we also knew that he cared very deeply about the paper. There wasn’t any sense that he was an absent father—on the other side, he taught all of us what a work ethic is, and how important it is to love what you do in life,” Anna told a reporter. She witnessed his passion for his work firsthand when she visited his office: meeting writers and seeing the papers getting printed, the smell of fresh ink wafting off the presses.
“There was always this sense of deadlines,” Anna told another interviewer. “This excitement about the news.” Sunday lunches were often dominated by family conversations about what was in the papers. “The gospel in our house was the newspaper,” Anna recalled.
Though Nonie had grown up close to her parents and enjoyed being with them, Anna later said her dad “came from quite a Victorian upbringing. I’m not sure his mother ever spoke to him.” But Nonie and Charles wanted to raise their kids more in an American manner, which meant being involved in their lives. In British households of a professional class, the children often ate dinner separately from their parents. In the Wintour household, Anna and her siblings were included in their parents’ dinners and social gatherings, which gave her access to Charles’s world. This glamorous and intellectual milieu, the excess of those parties, was normalized for Anna from a young age. And when famous journalists weren’t dropping by for dinners, the family would engage in their own high-level conversation around the dining table.
Under Charles, the Evening Standard’s influence proved that a tabloid could be both populist and sophisticated, and it became known as London’s best evening newspaper. (“On the front page you want the headless corpse found by the river,” he said, “but inside there must be at least one article that the Permanent Under-secretary at the Treasury cannot afford to miss.”) He hired foreign correspondents and ran liberal-leaning political coverage, while giving equal weight to arts and culture. His main goal was to attract a young readership to the paper, and when asked by a colleague about the secret of his success, he replied, “I just recruited young.” He valued his inexperienced staff’s input and was known to walk across the newsroom simply to ask a young writer which picture they preferred for the front page. It was no surprise that so many journalists wanted to work for him.
For a Fleet Street editor at the time, Charles was unusually good to female talent. “It was the beginning of second-wave feminism, so women’s rights were slightly fashionable but still really out there,” said Celia Brayfield, who finally got a writing job after applying about four times. Brayfield noticed when she started at the Evening Standard after working at the Daily Mail that she didn’t get wolf-whistled and catcalled when she was walking around the offices—a culture of restraint that could only have originated from on high. When she got pregnant as a freelancer, Charles insisted she take the same maternity leave as a staffer, even though she technically wasn’t entitled to the same benefits. That women were cheaper to hire was a given, but unlike many of his peers, Charles valued their talent.
Though Charles was supportive of and respected by his team, he was by no means easy to be around. His staff knew not to bother him before the first edition was set in the morning. In daily interactions, he was quiet, cold, and exacting. Charles had to make decisions constantly and therefore quickly. When he took members of his staff out to lunch once a year, he came with a notebook so he could consult a planned list of conversation topics. His speech, indicative of the British upper class, was clipped as if periods were inserted throughout his sentences: “Now let’s. Have. A discussion. About. That. Matter.” (The exception was his signature phrase, growled as one word, when someone made a mistake: “ForChrissakegetitrightnexttime!”) When a writer came into his huge office to show him a draft, he sat them at a distance from his desk, then put the article down, his forehead in his hand, and read the entire text without a word, making the person about as nervous and uncomfortable as possible. The middle-aged men on staff, who addressed Charles as “sir,” cowered in daily meetings where he ripped apart the previous day’s issues, demanding to know why one story ended abruptly and another was buried. When he walked by a workstation, Brayfield said, “He was so frightening that people would bend like a field of wheat under a wind as he went past. They would cringe over their typewriters, specifically from sheer authority.” Staff were thrilled when he offered a single word of praise—“excellent”—on the bottom of their copy.
Yet as terrifying as Charles was, he commanded respect, and they were eager to please him. “He was fascinating and we were all enthralled by him,” said Valerie Grove, who wrote for him. Despite how he came off to others, Anna saw her father as “warm and wonderful,” and didn’t understand why his work nickname was Chilly Charlie, defending him in a 1999 interview by saying, “It just seemed to have nothing to do with the person he was.” Many would later have the same sentiment about her.
Outside of work, he was less forbidding, especially at dinner parties. He loved gossip, and every so often a story about someone he knew would lead him to burst into a surprisingly loud and delightful laugh. Many nights, he and Nonie left their children with a nanny and went out to parties, plays, or the opera, believing appearances were an obligatory part of his job. A successful editor, he thought, must “accept more invitations than he wants and know more people than he likes.” Eventually Nonie’s attendance ebbed, and Charles went without her.
While Charles’s staff thought his success completely deserved, there remained an undercurrent that his rise was in part a reward for his stoicism, a level of militaristic discipline that his staff would recognize as uniquely Wintourian: to suppress a flood of tears, repress the shock, and continue with work as though every parent’s most unthinkable nightmare hadn’t just occurred. His staff would later notice this same bulletproof discipline in his eldest daughter.
Yet it would be a mistake to claim that Anna’s approach was entirely the product of her father. Arthur Schlesinger described Nonie as “bright, witty, and critical” with “a sharp eye for the weaknesses of others,” noting her cynical nature as a form of “self-protection, because I think she was extremely vulnerable.” Still, he added, “but she also was great fun to be with so long as one wasn’t the target.” Anna’s friends and colleagues would say the same thing about her.
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* Friends disagreed on whether Anna is introverted or extroverted herself.
During the 1960s, if something was cool, it came out of London. By the time Anna became a teenager, the city was in the throes of a “youthquake,” rationing and gloom replaced by hedonism, joy, and, of course, Beatlemania. Anna lived at the doorstep of it all in London’s St. John’s Wood district, home to Abbey Road Studios. “It was impossible not to be aware and excited, and to feel that the world belonged to the young,” Anna said.
Fashion was at the heart of this cultural transformation. Clothes for women who didn’t want to dress in stiff midcalf skirts and jackets like their mothers were finally available in boutiques sprouting up everywhere. Nothing more dramatically signified this shift than the miniskirt, which was regarded as scandalous even though the earliest iterations were just inches above the knee. (The Daily Mail declared that “a model girl’s best friend is a good pair of knees,” after designer Mary Quant started selling skirts a shocking “nearly 3 in. above the knee.”)
Barbara Hulanicki, a fashion illustrator by training, saw the desperation for new styles firsthand in 1964 when she designed a pink gingham minidress to sell through a newspaper advertisement for just 25 shillings. She received 17,000 orders for the dress, which was advertised as coming in only small and medium sizes. Hulanicki opened a pioneering boutique that she called Biba to sell even more of her affordable designs. She never made more than 500 of each item, and girls lined up outside every Saturday morning to shop before things sold out. Anna had little patience for lines, but managed to get there when the store opened to nab things before they vanished.
As much as fashion fascinated Anna, school did not. Though she “could probably become a sprinter of Olympic standard,” her father said, she did what she wanted—and running was not it.
In 1960, she had tested into one of London’s best private girls’ schools. “Queens College was a school for girls like me and Anna who didn’t want to go to university, but whose parents wanted them to,” said Emma Soames, a friend who attended separately from Anna. The school had rigorous academics (Anna excelled in English), and an exacting approach to discipline. Among the many things that were not allowed were chatting with friends in the hallway, speaking without being spoken to, asking too many questions, and wearing anything that wasn’t part of the uniform to keep warm. “It was so cold in the main hallway where we had prayers every morning that girls would faint. I developed frostbite in my feet as a child because I was so cold,” said Stacey Lee, a former classmate who befriended Anna. Anna soon decided to transfer to a new school, seemingly without concern for any friends left behind. “She just moved on,” said Lee. “She didn’t depend on people, or attach to people.”
In 1963, Anna started at the excellent North London Collegiate School. She wasn’t warmly welcomed by her new classmates, just about all of whom had attended since first grade, and who were so icy they didn’t even help Anna with directions around the school.
Another new girl having a similar problem was Vivienne Lasky. Lasky had moved from Berlin to London, where her New York–born father, Melvin, edited the influential pro-American (later revealed to be CIA-funded) Encounter magazine. She found Anna reserved in what Lasky felt was a very “British” sense; her manner of speaking was, like her father’s, clipped. But she also sensed that Anna wanted to be noticed on her own terms: she stood like a model in a fashion spread—with her back rounded and shoulders hiked, exhibiting a certain fashionable confidence.
Even though Lasky became her friend, Anna could be brusque. She made unsparing comments to Lasky about other people’s appearances—most notably frizzy, natural curls, which she abhorred, and her fellow students who, Anna concluded, having been stuck nearly their entire childhoods in brown uniforms, lacked any “idea of color or style.”
Yet such critiques were off-limits when it came to Anna’s family. Her dad went to work every day in the typical Fleet Street man’s uniform of a white shirt, the sleeves rolled up to the elbow, and a tie. Her sister, Nora, didn’t have perfectly straight hair like Anna’s, or put much effort into caring for it. Her mom’s clothes likely came from a middle-market retailer. (Later, when Anna entered the workforce, she bought her mom a navy skirt from Browns, a designer store in London’s upscale Mayfair neighborhood. Nonie only learned that the poorly fitting skirt cost more than £100 when she went to the store to return it.)
Anna, stuck in her school uniform for most of her waking hours, kept up with everything new and trendy by reading voraciously—books, newspapers (as many as eight on Sundays), magazines, literary journals. Anna especially loved Seventeen, which Nonie’s mom sent her from the US, the covers always featuring a pretty girl, often with flipped hair, in a graphic print or kicky dress. The cover lines touted fashion and beauty, but the issues had more, everything from diet tips to teen correspondents interviewing then–attorney general Robert F. Kennedy. “[Seventeen] was just my dream,” Anna confessed years later. “I couldn’t wait for it to come every month.”
For Anna, it wasn’t enough to just look good; she wanted to be admired as the best-dressed person in the room, Lasky said. That notice was essential to her, and it spoke of a contradiction. Her life at home was one of culturally elitist comfort and, through Charles, power. As Anna entered adolescence, she would be known wherever she went in London as the daughter of the celebrated newspaper editor Charles Wintour. Yet outside the house she could feel invisible, ignored by her classmates, her individuality suffocated by the sameness of the uniform—not just the wretched ones she had to wear at school, but the general blah that had characterized most clothing in Britain. Standing out was more than a tactic for immediate acknowledgment—it was an assertion that someone could escape not merely the beige and brown but also, in her case, the notions of what it meant to be a Wintour. Her beauty regimen included taking yeast pills from the same trichologist, Philip Kingsley, her father saw to prevent his hair loss, never mind that her hair was perfect all on its own; visits to a dermatologist, even though her skin was nearly flawless; and buying cream by the high-end brand Charles of the Ritz to address her occasional blemish, though she never wore a lot of makeup. While at North London Collegiate, Anna went to Vidal Sassoon, where the bob haircut that became emblematic of the era had originated. She had her thick, naturally straight brown hair cut shorter and got blunt bangs so long they brushed her eyelashes. The whole point of the look was to have perfect, freshly cut ends and bangs—mandating frequent trims, but she had no problem maintaining it with regular trips to Leonard of Mayfair, the salon to which Sassoon stylists defected. The style, though it became her signature, was completely unremarkable in London, where young women everywhere had the same haircut.
Anna usually didn’t directly tell someone she disagreed with their choices—of what to wear or eat, or how to act—but she had a way of making people feel they should be a certain way, a way that was, really, more like her. The look of the period was skinny. “We wanted to be Twiggy thin,” said Lasky—which is to say, really thin. Anna and Lasky ate little more than a Granny Smith apple during the school day. When Anna would invite Lasky over and cook her favorite foods, like cheesecake, but not eat any of it herself, her restraint started to make Lasky feel like she was doing something wrong—something those close to Anna would often experience—and that she needed to do more not so much to keep up the look itself but to maintain Anna’s approval. After it came out in 1964, Anna adhered to The Drinking Man’s Diet: How to Lose Weight with a Minimum of Willpower, which boasted of a one-sentence regimen: “Eat fewer than 60 grams of carbohydrates a day.”
Anna loved going over to Lasky’s house and talking to her parents. Her mother was a beautiful, slender ex-ballerina who wore designer clothing and fed the girls gourmet food. “Nonie was terribly aware of this crush that Anna had on my mother,” recalled Lasky. “They were opposites. My mother never left the house without wearing a couture suit. She wore ropes and ropes of pearls. She never weighed more than eighty-five pounds.”
Though Anna’s judgments of others were ruthless, she was probably hardest on herself. She once bought an expensive outfit to wear to her cousin’s wedding, including a pink skirt with a floral jacket. When she got the pictures back, she was distraught. “Well, I just don’t know about my legs,” she said.” When she found a tape measure and checked the width of both her own and Lasky’s knees, she was horrified to learn Lasky’s were smaller. It was as if she felt forever doomed by the tiny difference. Lasky pointed out that Anna’s weight hasn’t appeared to change since she was eighteen years old.
Even once settled at school, Anna never found much of a social circle there beyond Lasky. In interviews, Anna has described her child self as shy, but friends are divided on whether or not she is. They agreed, at least, that she was silent. Lasky didn’t see her as shy. “She didn’t want to be part of a group that existed. She wanted to be in her own rarefied air,” she said, adding, “She wouldn’t go out of her way to sort of connect with this one and that one unless it [was] truly necessary. That’s part of that mystique.”
During Anna’s teen years, Charles and Nonie’s marriage soured, probably partly because of his affairs, and likely from the irreparable damage to their relationship from the fallout of Gerald’s death. The dinner gatherings became increasingly tense, their guests dreading the prospect of the couple arguing. Mary Kenny, who was working for Charles at the time, said their bickering at dinner was so bad that she got the distinct impression that Charles and Nonie were actually trying to embarrass each other. “It was terrible, really, being with them,” she said.
But at least the visitors’ exposure to their tortured relationship was limited. Anna had to live with it. Lasky and Anna adored their dads and were horrified to come to a realization that their fathers weren’t faithful to their mothers. How could their dads—their wonderful dads, whom they idolized—be capable of cheating? Plus, Anna surely recognized that the people who most impressed her venerated dad were not the sort devoted to, say, selflessly helping pregnant teens, but women who were prominent in publishing, just like him.
When Anna was around fifteen, the Wintours moved to a larger house in Kensington where she got the basement apartment with its own entrance, totally separated from the rest of the house. One long wall of the apartment contained a white bookcase (among the furniture her parents had purchased from Habitat, a hip interiors store), stuffed with books. Her large, spare bedroom was done in toile, blue and white, the apartment not only a sanctuary of her own good taste, but also likely sparing her from overhearing her parents.
Anna’s academic disinterest was increasingly clear during her second year at North London. She got to study under Peggy Angus, a famous artist with two works in the National Portrait Gallery, further inspiring an interest in art that would influence Anna as a young fashion editor and ultimately help get her a meeting with Vogue. But most of the curriculum bored her. Occasionally, without any consequence, she and Lasky forged notes saying they were sick or had to go to the doctor and went to Leicester Square to shop. (They changed out of their loathed uniforms in public bathrooms.) At the end of the school week, Anna couldn’t wait to get dressed to go out. She and Lasky took the tube home, washed up, changed into their night looks (usually minis), and watched the live music show Ready Steady Go!. (Its slogan was “The weekend starts here!”) At 11 p.m., the pair would hail a cab to go to one of their favorite clubs. As Anna described in an article in North London Collegiate’s student magazine, the Garrison’s crowd was young blondes trying to impress businessmen (boring); the Scotch of St. James had a better, more mixed patronage, but was too packed (uncomfortable); Dolly’s, where “the titled and the rich chat amiably with the famous and the notorious and the debs and the dukes dance side by side with pop stars and their camp followers” had “the most way-out outfits” and “the kinkiest gear. . . . With a Beatle and a Stone or two and Cathy McGowan [the host of Ready Steady Go!] thrown in, what more could anyone ask?”
Bouncers didn’t check IDs, but Anna and Lasky weren’t trying to get drunk—they had a Shirley Temple or a Coke and left in an hour or less, just enough time to see and be seen and still get enough sleep before going to Biba early the next morning. “Both of our families were very trusting. We were not promiscuous girls. We were not crazy girls,” said Lasky. And for Anna, going out was never about going wild. Visiting the clubs was more about reconnaissance than excess. Amidst a crowd of the fashionable, she was studying.
Anna’s formal education ended when she was sixteen years old, departing North London Collegiate before completing her final year.* University had been an important part of her parents’ lives, but she had no reason to go to Oxford or Cambridge (the only real point of spending a fourth year at North London) if she aspired to work in fashion. Years later, Anna told her close friend the playwright David Hare, “I was so desperate to get out in the world and get on with things.” She wanted to work.
At the time, it was not unusual for British teenagers to leave school early, with some women going on to finishing school to prepare for domestic life, or to secretarial school.** Unsurprisingly, Nonie and Charles were less than happy about Anna’s decision. “I don’t think it was snobbishness so much as the Wintours just felt that education was . . . a tool that could absolutely change your life,” Lasky said. But Anna’s parents accepted her decision, as far as Lasky could tell. “They never threw it in her face.”
On the other hand, her siblings shared her parents’ interest in politics and social issues, and all attended prestigious universities. Anna felt like the black sheep of the family. “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. I’ve always been a joke in my family. They’ve always thought I am deeply unserious. My sister would always ring up and say: ‘Where is Anna—is she at the hairdresser or the drycleaner’s?’ It’s not their world,” she later recalled. But while her siblings didn’t understand her interest in fashion, Charles seemed to appreciate it. Fashion was part of the culture the Evening Standard covered, so he had to keep up with it somewhat. But he also cared that fashion exhilarated Anna, who seemed to many to be his favorite child.
Charles denied that he ever pushed Anna into a media career—“Anna said she felt that what I was doing was exciting . . . ,” he said—but in fact, she knew that her dad wanted her to go into journalism. (He would sometimes ask her if she’d read certain articles and what she thought of them, almost as if training her for her future responsibilities.)
Yet she was wary, half in and half out. “I certainly grew up knowing that being in publishing was something I wanted to do,” she told journalist George Wayne, but “chose to go into magazines because that wasn’t so much his world.” Still, some twenty years into her Vogue editorship, she said Charles was ultimately her primary influence. “I think my father really decided for me that I should work in fashion. 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 you want to be editor of Vogue, of course.’ And that was it, it was decided.”
Her determination lit up like a match.
A few months after Anna ended her education, her grandfather Ralph Baker died. He left behind an estate for his surviving wife,