Anna Wintour has long earned the sobriquet ‘The Ice Queen’ not only for her haughty and imperious air, but for the relentless and sometimes cruel and brutal way in which she conducts her editorial meetings, arranges her social calendar, and in particular, the planning of the Met Gala— but despite this intimidating reputation in 1999, the Ice Queen began to melt and fled her famous party in tears.
It was the second and only time after her mother’s death that the late Andre Leon Talley (Wintour’s colleague of 30 years), witnessed the legendary iceberg lose composure.
Despite the razzle-dazzle of ‘fashion’s most celebrated night’, the infamously reserved ‘Ice Queen’, who was wearing a custom John Galiano dress, left the party early, with a flood of ‘mascara-laced tears running down her face.’ She had just suffered a nasty divorce after a torrid affair with her then boyfriend, Shelby Bryan, and this was their first public outing.
Today, on the heels of the star-studded event last night, a newly published biography written by Amy Odell details the meticulous and almost obsessive planning that goes into ‘the red carpet fashion event to end all red carpet fashion events.’
Jam packed with juicy details, Odell chronicles how Wintour turned a staid fundraiser for the Metropolitan Museum of Art’s Costume Institute into a profound and far reaching cultural event – pulled off by the Vogue Empress’ battalion of planners and assistants under her decisive and punishing scrutiny.
It’s the hottest and most exclusive ticket in town. The high-profile fundraising gala has been hosted by Vogue’s editor-in-chief Wintour, 72, for nearly 30 years now, and it marks the opening of the Costume Institute’s annual fashion exhibit on the Upper East Side of Manhattan.
With her exacting taste and attention to detail, Wintour has become a powerful arbiter of deciding, ‘who’s in’ and ‘who’s out.’ For instance, the Hilton sisters, have never been invited to the party, despite being extremely relevant in the early aughts. Until 2013, the Kardashians were banned too.
No money in the world could guarantee a ticket. ‘You could have had a billion dollars, you were not going to get that ticket. . . . There had to be a reason for you to be in that room,’ explained former Met Gala planner Stephanie Winston Wolkoff.
During the party, Wintour wants Vogue staff to know every single detail about each celebrity’s arrival – including when they’re going to get there (every star has their own prearranged time), what car they’re going to come in, and what they’re wearing.
According to Odell, Wintour controls every aspect of the 700-person guest list, and decides who is allowed ‘in’ and who is ‘out’
She has say in every aspect of the party and leaves no stone unturned: from the supervision of the seating chart (which she has turned into an exact science), to the exorbitantly expensive decorations, to the dinner menu (no parsley, garlic, onions, chives or fish), and how the food is presented on the plate based on the color pallet.
She’s always been particular about the food, ‘though at tastings, she barely tasted,’ said Wolkoff. Her favorite items were lamb chops, steak, and French haricot verts.
‘But the dish she seemed to love serving at Vogue events over any other was chicken pot pie, ideal to Anna because it’s a one-course meal that has everything (protein, vegetables, etc.). For dessert, she loved crème brûlée.’
At dinner, everything had been thought of down to the backless chairs for guests who wore gowns that wouldn’t fit into a regular seat. When Kim Kardashian wore a skin tight latex Thierry Mugler dress in 2019, Wintour kept asking to Teen Vogue director, Lisa Love, ‘Can you please tell her to sit down?’ Love had to explain that, actually, Kardashian physically couldn’t sit.
Her directives in the past have often been so absurd ‘the Met team just laughs them off,’ Odell reported.
Two other people close to Wintour recalled a time that she asked the museum to cover up the historical Temple of Dendur – a 2,000-year-old Egyptian temple that she thought was an eyesore. When they didn’t agree, she decided to cover it with Katy Perry’s stage.
‘Once, when walking through the Egyptian galleries, where the display cases were empty because they were being replaced, she turned to the Met team and said, ‘Where is she? Yes, you—can you go into the basement and just bring up a bunch of art and put it in these cases?”
Today’s table prices cost a minimum of $275,000 and individual tickets are $42,700. Wintour personally selects the 700-person guest list, that includes the biggest names in fashion, as well as emerging designers, Vogue cover stars, famous model, ingenues and actors from big films.
‘Anna created the whole entertainment and fashion world that was on the red carpet of the gala,’ said Wolkoff in the book.
But according to author Amy Odell, it wasn’t always that way. Today’s event is almost ‘unrecognizable’ compared to the first party Wintour hosted in 1995.
Back then, tables only cost $1,000 and were open to anybody willing to foot the bill. A post dinner dance party in the museum’s Temple of Dendur (built in 15 B.C.) was offered for the price of $150 to a younger crowd that often got so raucous, it ended in guests smoking, drinking and puking near the two-millennia-old monument. The dance party was officially axed a few years later after a Met staffer witnessed debauched women peeing in the Great Hall.
Anna was also always concerned about the behavior of everyone who might be there, from guests to waitstaff to performers,’ said Wolkoff. According to another Vogue editor, if Wintour deemed that a guest was behaving badly, it would affect their prospects for Vogue coverage down the line.
Hyper aware of the image, Wintour made sure staffers working the event also looked the part. ‘God forbid if they’re fat, if they are unsightly, they have to go,’ said former Vogue copywriter, Sarah Van Sicklen.
In 1995, Wintour ordered apron dresses from Calvin Klein for her staff to wear. The women were stationed throughout the space, their job to direct guests to the bar or bathroom.
Today, a team of Vogue writers and digital staff work in the basement of them museum, furiously typing away at laptops to publish content to the fashion magazine’s website.
In 2018, Vogue went to the extent of hiring a ‘movement coach’ to direct guests in eight-second videos that showcased their outfits for Instagram.
The basement workers are also expected to wear formal attire, and are usually allowed upstairs for a few minutes to watch the performance. All dresses on Vogue staff are photographed ahead of the event and given to Wintour’s senior fashion editors for approval.
1999 was the year that Wintour took over as chairperson and host of the Met Gala (which was hosted in December at the time). She had been coming off a particularly tumultuous year in her personal life.
News of her torrid affair with the married Texas financier, Shelby Bryan had splashed across the tabloids throughout the summer. ‘I didn’t like it. I was married,’ said Bryan in the book. ‘The press, as it turned out, I guess was correct, but they were getting ahead of our relationship.’
Wintour finalized her divorce with child psychologist, David Schaffer in the fall, and went straight into the planning the Met Gala as its newly minted chairperson.
Critics denounced the exhibits as commercialism masquerading as art. Wintour focused on fashion brands, who came in with big checks and forced society donors out of the way. Which Odell said, left wealthy New Yorkers ‘seriously disgruntled.’ Before adding that ‘the Met Gala would never be the same.’
The theme was ‘Frock ‘n’ Roll’ and the editor asked Tommy Hilfiger to be the sponsor after the designer had dubbed 1999 his ‘Year of Music,’ making Lenny Kravitz the face of his ad campaign and putting on two elaborate rock-themed fashion shows with performances by Sugar Ray and the band Bush.
At the time, Wintour was in the process of replacing models with celebrity faces on the covers of Vogue and she liked Hilfiger’s connection to the Hollywood set. Teen heartthrob, Jennifer Love Hewitt was the crown jewel of the evening, and was allowed (with the permission of Anna) to bring her mother as her date.
‘A Hilfiger partner, however, was encouraged not to bring family and friends, but to host glamorous people, like models from the Hilfiger ads,’ wrote Odell.
Collaborating with the Rock & Roll Hall of Fame in Cleveland proved to be a more difficult endeavor than originally expected.
Prince allegedly wanted a cut of the Met’s ticket sales. Madonna wanted her clothes to be in their own case, specifically not next to Britney Spears’s.
When securing Madonna’s famous cone bra designed by Jean Paul Gaultier was in limbo, Wintour told the curator Jeff Daly, ‘I don’t care, figure it out. Make Madonna happy, make Michael Jackson’s people happy, make the Beatles happy.’
The list included the regular society dames: C. Z. Guest, Jayne Wrightsman, and Nan Kempner, as well as fashion luminaries such as Carolina Herrera and Oscar de la Renta.
Sean ‘Puff Daddy’ Combs performed, with his girlfriend, Jennifer Lopez in tow. Causing Henry Kissinger to remark, ‘Who is this fluff daddy?’
Also present were: Whitney Houston and Bobby Brown, Christina Ricci, Maxwell, Elizabeth Hurley, Gwyneth Paltrow and her dad Bruce, Steven Tyler, Tom Ford, Missy Elliott, and Mary J. Blige.
Lil’ Kim wore a studded pink bikini, causing The Washington Post to remark that it ‘would have caused the windows in the room to fog up, if there had been any.’
‘It was the flashiest and most shocking party the Met had ever thrown,’ says Odell. Long gone were the wooden Uptown New York galas of years past, Wintour cemented her future as its reigning Empress.
The party raised $3million for the museum, but despite its raging success, Wintour ended the night tears. Having barely slept in two days, Andre Leon Talley, found her leaning against the wall, in her custom John Galliano gown, wrapped in red fox fur, with ‘mascara-laced tears running down her face.’
The evening was intended to be her first public outing with then boyfriend, Shelby Bryan, but he left the event early. ‘It was not correct for him to make her cry like that in public,’ said Talley. ‘She was vulnerable.’
Oscar de la Renta escorted the fragile editor to her car by sneaking out the back of the museum. For Talley, it was only the second time he had seen Wintour breakdown in the thirty years working closely side by side.
In 2003, Wintour met her match when she asked Tom Ford to be her co-host. As far as details go, Ford was preoccupied with the appearance of the waiters working the event. He demanded their hair be perfectly slicked back and hired staff ‘like a casting call,’ Wolkoff said.
The designer also wanted to approve the menu and table settings, so they arranged for a chef to fly to London for a demonstration. ‘What we served had to look right on the plate together. I not only had to see it plated, but if the colors didn’t work together of the vegetables and the whatever, they had to go,’ Ford told Odell.
When Wintour fussed over Ford’s expulsion of carrots, he told her: ‘They’re orange, they can’t go next to that color, that doesn’t look good. It’s just not going to happen.’
She attended that year’s
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