Inside Anna Wintour's Mysterious Private World

If you saw Anna Wintour in the elevator, you did not talk to her. In fact, you avoided eye contact altogether.

Sure, if you were Sarah Jessica Parker or Gisele Bündchen or Hillary Clinton, you were probably in the elevator to see her. But if you were just some lower-level staffer at Vogue or otherwise visiting the venerable publication's Manhattan headquarters...please, courteously look away.

That was the impression outside the hallowed halls of Vogue in 2004, anyway, a year after the novel The Devil Wears Prada skewered the fashion magazine business and the character of "Runway" editor Miranda Priestley—whom most people assumed was a thinly veiled take on Wintour. A chic, silver-haired Meryl Streep would further immortalize the character in the 2006 film.

"It wasn't a one-to-one portrayal," author Lauren Weisberger, who spent 11 months working as Wintour's assistant, told the Daily Mail in 2010. "But of course my time at Vogue informed the book, there's no denying that."

Ironically, though the book spent six months on the New York Times Best Seller list and the movie rights were optioned immediately, it was Weisberger's heroine, Andy Sachs (and therefore Weisberger), who was criticized for coming off as just as much of a snob as anyone at Runway, the Ivy League grad and aspiring Serious Journalist who thought she was too good for the frivolities of the fashion world. 

And Miranda Priestley actually came off as kind of a badass—and a recognizably human badass at that.

"I...wanted a scene where she is without her armor, the unpeeled scene in the hotel room—just to see that face without it protective glaze, to glimpse the woman in the businesswoman," Streep recalled to Variety for the film's 10th anniversary in 2016. Having always insisted that she never tried to play Wintour, per se, she channeled a variety of men.

"The voice I got from Clint Eastwood," the actress, who scored one of her record 21 Oscar nominations for her performance, said. "He never, ever, ever raises his voice and everyone has to lean in to listen, and he is automatically the most powerful person in the room. But he is not funny. That I stole from Mike Nichols. The way the cruelest cutting remark, if it is delivered with a tiny self-amused curlicue of irony, is the most effective instruction, the most memorable correction, because everyone laughs, even the target. The walk, I'm afraid, is mine."

Streep, incidentally, was on the December 2010 cover of Vogue, so whatever feelings her performance engendered were not hard.

"It was entertainment," Wintour said of the film, telling 60 Minutes in 2009, "It was not a true rendition of what happens within this magazine."

But considering how much Streep put into conjuring this larger-than-life character, you can imagine how hard the Anna Wintour had to work to ascend to her real-life role running the 131-year-old institution that is Vogue (duties she's juggled since 2020 with being Global Chief Content Officer of publisher Condé Nast, as well as artistic director since 2013).

"I grew up at a time when women still left the dinner table so men could smoke their cigars and talk about the real issues of the day," she told the Financial Times in an interview published Sept. 22.

No one has ever suggested that Wintour isn't a tough boss, but people continue to want to be part of the still vibrant and glamorous (if not as much taste-dictating) world that "Nuclear Wintour"—a holdover nickname from her days in charge of British Vogue—has cultivated in her 35 years atop Vogue's masthead.

"If I'm such a bitch then they must really be a glutton for punishment, because they're still here," Wintour noted of the people who'd worked for her for 15 or 20 years. Simply, "there's on-duty time and there's off-duty time"—and when they're on duty, she expects those around her at Vogue to be singularly focused, as she is, on the magazine.

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

And that ideal certainly never goes out of style.

Ironically, rumors started swirling in early 2018 that the Met Gala that May, the annual $30,000-a-ticket, A-list affair that has usurped the Oscars as fashion's most exciting red carpet (former Vogue creative director Grace Coddington credited Wintour with seeing "the celebrity thing coming before everyone else did"), would be her last as Vogue editor in chief.

If true, it was going to be the end of an era. A "host of stunned sources" told Page Six that Wintour could leave as early as that summer following her daughter Bee Shaffer's wedding. 

Five years later, Wintour, who's turning 74 on Nov. 3, remains at the helm of it all.

"I love what I do," she told the Financial Times. "I am consistently challenged by it."

In 2020, in the wake of Vogue coming under fire for a historic last of diversity in its office and within its pages, Wintour was promoted to global editorial director with a promise to do better at all of it.

"If you go back to when I was a young girl growing up in Britain, and I went for my first job, it was considered a great thing if we reached an audience of 90,000 people with a monthly magazine," Wintour told CNN's Christiane Amanpour in April 2019. "Now we have, I believe, 22 million followers on Instagram alone at Vogue US. So we are talking to men and women all over the world ... in so many different ways [and] in a way that we couldn't possibly have imagined even 10 years ago, 15 years ago."

It's 47.1 million followers now and, as she told the FT, her job since 2020 has been to "make sure everyone [across all of Vogue's editions around the world] felt it was a different day, and that we were all working together as a global network. 

But Wintour is closer to the end of her tenure than she is to the beginning. Coddington, whom Wintour called "the heart and soul of the magazine," stepped down in 2016 after 28 years as creative director.

Asked during a talk at the Vogue Festival in London in 2016 how she got along with someone as dominant as Wintour, the fiery-haired Coddington quipped, "I'm older than she is."

More seriously, Coddington told 60 Minutes of Wintour, "I think she enjoys being not completely approachable." And in her 2012 book Grace: A Memoir, she remembered realizing decades beforehand "how much significance Anna places on willpower trumping feelings."

Let's just say, Wintour doesn't wear those gigantic black sunglasses 98 percent of the time solely to shield her eyes from UV rays. 

"I'm very driven by what I do," she told 60 Minutes' Morley Safer in 2009, in response to some of the choice descriptors she's been called over the years, including "Darth Vader in a Frock." "I am certainly very competitive. What else am I—needy? Probably very needy, yes. A bitch? Um, well, I..." she smiled, thinking. "I hope I'm not. I try not to be. But I like people who represent the best of what they do, and if that turns you into a perfectionist then maybe I am."

Maybe because she's simply more comfortable shedding her armor these days after being at the pinnacle of her profession for so long, the smile she flashed readily in the 2009 documentary The September Issue has been making substantially more public appearances in recent years.

And though you'll still be hard-pressed to capture the elusive smile-with-teeth-and-no-sunglasses in the wild (it did occur while she was being honored in April at the Fashion Scholarship Fund Gala), the often stone-faced Fashion Week fixture does enjoy poking fun at her own severe image.

She doesn't have a personal Instagram account or anything, but a few years ago she opened up her bright corner office at One World Trade Center, full of fresh blooms, framed photographs and the sleek desk where so many decisions are made, to answer Vogue's 73 Questions. (She has Starbucks every morning, she doesn't drink alcohol, Hugh Jackman is her favorite action star, you'll never catch her in head-to-toe black, her favorite vacation spot is home and all the rumors about her are true.)

In other lighthearted moments, Wintour was revealed as the comedy mastermind behind Saturday Night Live and Seinfeld in a brilliant bit on Late Night With Seth Meyers, where daughter Bee used to work as a segment producer. In 2016 she swapped lives with Vogue cover girl Amy Schumer for a day and did a set at the Comedy Store. And in 2018 last year she sat down with James Corden (her favorite comedian) for "Spill Your Guts or Fill Your Guts," during which she took a bite of bacon-wrapped pizza rather than pronounce Ralph Lauren or Marc Jacobs better than the other.

Not exactly the ice queen everyone's talking about—though she did wear sunglasses a lot of the time.

"They are seriously useful," Wintour explained to 60 Minutes about the reason she's almost never without a pair, usually Chanel and, nowadays at least, corrective. "I can sit in a show and if I am bored out of my mind, nobody will notice… At this point, they have become, really, armor." Moreover, she told CNN's Amanpour, they're "incredibly useful because you avoid people knowing what you're thinking about."

Even Queen Elizabeth II didn't get a look at the whites of Wintour's green eyes when they sat next to each other at London Fashion Week in February 2019, a move that didn't sit well with royal enthusiasts but which the monarch herself didn't seem to mind. If anyone was going to understand a powerful woman who's set in her ways, it was the late queen.

Wintour has said she rises at 5 a.m. and loves to both play and watch tennis as often as possible—as evidenced by her annual presence at the U.S. Open, where for years she cheered for favorite Roger Federer—and then made him co-chair of the Met Gala after he retired.

In addition to her weekend home in Mastic, N.Y., on Long Island, she owns a historic four-story townhouse in Greenwich Village. She's been sporting the same haircut with thick bangs since at least the 1980s—the "Anna bob" is obviously an institution. (Though the magazine business has changed a lot over the past decade, 60 Minutes reported that Condé Nast picked up the tab for her makeup and those impeccable blowouts every day of the week.) She's invariably in skirts or dresses and loves a good print (or two).

And for the past 25 years she has primarily worn custom-designed nude Manolo Blahnik slingback sandals, occasionally differing in texture and tone but primarily the same style, whether she's at the office or the Met Gala. (She does have boots, for blustery days in New York, Paris, etc.)

While that has mystified those who would assume that her shoe closet would be the 8th wonder of the world, it makes sense if she'd rather keep the spotlight on her outfit. Or maybe Wintour's toes just need to breathe!

"I never comment on the number of pairs anyone orders, but Anna always likes to have her shoes, like everything in her wardrobe, impeccable at all times," Blahnik, who designed the not-available-to-the-public "A.W." for Wintour, told Vogue in 2011. "I often talk to Anna about what's inspiring her that particular season and what she's ordered for her wardrobe. Anna has fantastic legs, and her feet are always meticulously groomed."

Talking to the Telegraph in 2016, Blahnik called Wintour, who's featured prominently in his coffee table book Fleeting Gestures and Obsessions and the documentary The Boy Who Made Shoes for Lizards, "a divine woman. So normal and loyal. We went to the movies together all the time in New York, because we loved movies. So we went at 9 o'clock in the morning. This was before she was at Vogue. No time now, poor thing."

As for her personal life, Wintour is the daughter of Charles Wintour, who edited London's Evening Standard, and Eleanor Baker, a film critic, and she was named after her maternal grandmother. Her brother Patrick Wintour is diplomatic editor for The Guardian and sister Nora Wintour is a writer and policy advisor on industrial relations and labor rights. Another brother, Gerald, died in a bicycle accident at 14.

After leaving school at 16 ("a combination of being a lazy student and having brothers and sisters who were very academic," Wintour told the FT), she worked on the sales floor at the department stores Biba and Harrods. Her father helped her get her first editorial job at fashion publication Harper's & Queen in London, and then she moved to New York in the 1970s. Stints at Harper's Bazaar and New York led to her being hired as Vogue's creative director.

In 1984, she married pediatric psychiatrist David Shaffer, so after she was named editor of British Vogue the following year she racked up a lot of air miles. 

"My husband was chief of child psychiatry at Columbia, and he quite rightly didn't want to give up his position," she recalled. "So we commuted quite a bit. I had my son Charlie [in 1985], and then I was pregnant with my daughter [born in 1987], so I felt like I was just endlessly pregnant."

Tired of the commute, she moved back to New York and edited House & Garden for a few months before she was offered the top job at Vogue. The November 1988 cover marked the first of her ongoing tenure.

She and Shaffer divorced in 1999—in the wake of Wintour having already moved on with telecommunications tycoon Shelby Bryan, who was also married when they met at the Benefit Ball for the New York Ballet in 1997.

Never one to really talk about her private life, then or now, Wintour told New York magazine in 1999, "There are certain things that no one wants to read about in the tabloid press...You know that your friends and your family have one vision, and if the outside world has another, then that's just something that you just don't focus on."

Bryan, who hails from Houston, similarly told Texas Monthly in 1999, "There's an old-fashioned view that your personal life should be kept private, and that's my view."

The initially scandalous coupling naturally prompted a wave of finger-waving, as well as the usual speculation that perhaps Wintour wouldn't be in her lofty position at Vogue much longer.

"What I feel bad about is people trying to use whatever situation is going on in her life to attack her professionally," Oscar de la Renta told New York as rumors swirled that her bosses at Condé Nast could be losing faith in her. "Is she giving up her job? Is she not doing as good a job? It's easy to try to beat someone down. But anyone who'd try to do that to her would be a fool."

Isaac Mizrahi viewed Wintour's romance with Bryan most enthusiastically, saying, "She's never seemed so giggly and sparkly-eyed and beautiful and happy. Listen, this doesn't look like a crisis to me. To me, it looks like a liberation!"

Wintour and Bryan were together at the U.S. Open in 2018, but no one was the wiser when they eventually split up, People reporting in October 2020 that Wintour and Bryan had gone their separate ways some years beforehand.

Wintour's photo op at the 2023 Met Gala with Bill Nighy prompted a cycle of speculation that they were an item making their red carpet debut, but a rep for the Oscar-nominated British actor confirmed to E! News afterward that "they have simply been great friends for two decade" and were not in a relationship. (Nighy shares actress daughter Mary Nighy with his former longtime partner Diana Quick.)

Meanwhile, Wintour's family has continued to grow: Daughter Bee married director-photographer Francesco Carrozzini, son of the late Vogue Italia editor-in-chief Franca Sozzani, in July 2018—twice, first on Long Island, N.Y., and again in Portofino, Italy.

In 2014, Wintour hosted Charles' wedding to Elizabeth Cordry at her house in Mastic. The bride wore Oscar de la Renta, the non-devilish bridesmaids wore Prada, the flower girls wore Alexander McQueen, and the mother of the groom, glimpsed briefly from behind in one of the pictures published on Vogue.com, wore Chanel.

Charles and Elizabeth welcomed daughter Caroline Anne Shaffer in March 2017 and her sister Ella was born in February 2019, while Bee and Francesco had son Oliver in October 2021.

Wintour remains synonymous with Vogue, but she hasn't lived the 24/7 publishing lifestyle for some time, nowadays leaving work at what she described to the FT as a "reasonable hour" and spending weekends with her family in Mastic.

"For me, when I'm home with my kids and the grandchildren and my friends at home, we don't talk about work," she said. "We play tennis, and stupid games. That's my solace."

And while Wintour is already thinking about next year's Met Gala theme, you can relive the best fashion moments from this year's event right here:

In Valentino.

In Chenpeng Studio.

In custom Valentino.

In custom Schiaparelli.

In custom Marc Jacobs.

In Gucci.

In vintage Chanel and Tiffany & Co. jewelry.

In custom Givenchy.

In custom Karl Lagerfeld and Cartier jewelry.

In Valentino.

In custom Balmain and Cartier jewelry.

In custom Michael Kors.

In Thom Browne.

In Atelier Versace.

In custom Vera Wang and Cartier jewelry.

In Chanel.

In custom Michael Kors Collection.

In Chloé and Cartier jewelry.

In custom Christopher John Rogers and De Beers jewelry.

In custom Jacquemus.

In Oscar de la Renta.

In Gucci.

In Gucci and De Beers jewelry.

In custom Schiaparelli.

In Chanel.

In Harris Reed.

In custom Michael Kors.

In custom Oscar de la Renta and Cartier jewelry.

In Prabal Gurung and De Beers jewelry.

In custom Sergio Hudson.

(Originally published May 7, 2018, at 3 a.m. PT)