‘Oh my god’: The historic morning Anna Wintour let down her guard

This story is part of the June 5 edition, appearing in Sunday Life.See all 13 stories.

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 at about 10.30 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 before 5am, exercised at 5.30 or 6am (depending on whether she played her twice-weekly tennis or worked out with her trainer), sat for 30 minutes for professional hair and make-up, 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.

Wintour at a 1998 party celebrating Oprah on the cover. Credit: Getty Images

Her requests to 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.

Wintour at a Swiss tennis tournament in 2019.Credit: Getty Images

At 7.30 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.

Wintour with the Queen in 2018.Credit: Getty Images

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 fibre 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?”

“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?”

“With the bitter election now in the rear-view 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?”

Wintour with Karl Lagerfeld in 1993.Credit: Getty Images

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, she hadn’t begun a formal process for filling those positions, an adviser said. It was also unclear whether Anna 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, 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.”

Wintour sporting those iconic sunnies in 1989.Credit: Getty Images

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 not dwell on what could have been, and that pattern held. “But he’s the president,” she 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, was out of the office: “Oh my god – Anna just cried in front of everyone.”

“Oh my god – Anna just cried in front of everyone.”

Before Trump was inaugurated, Anna begrudgingly reached out. He’d 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 chequebook. Via his daughter Ivanka, a long-time acquaintance, she arranged to meet the president-elect at Trump Tower. Donald told his wife Melania that Anna was coming to see him.

Wintour at a 2021 London fashion dinner.Credit: Getty Images

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 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 f--k about Vogue or any other magazine,” she said.

But, Winston Wolkoff believed, she did give a f--k about Vogue. She wanted the cover once more.

Edited extract from Anna: The Biography (Allen & Unwin) by Amy Odell, out now.

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