The Untold Truth Of Anna Wintour

As iconic and well-known as Vogue editor-in-chief Anna Wintour is in the fashion industry, she's also largely a mystery. While her huge influence on the fashion world is no secret, much of her personal life is. Read on to find out what really goes on behind those dark sunglasses and signature haircut.

At first glance, Wintour appears standoffish and even a little icy. As described by New York magazine writer Amy Larocca, this "performative silence" only adds to Wintour's allure.

However, people who really know Wintour would likely tell you her mysteriousness is not a performance, but rather an effect of her shyness. According to journalist Amy Odell, who met Wintour during a job interview, "Anna did seem shy." In her memoir, Tales From The Back Row, Odell describes how she reached out to an ex-Vogue employee before the interview to get some insight. "She...cautioned me not to be thrown by Anna, who 'is shy and of few words more than she's mean or anything like that,'" Odell wrote. "'She won't bother to warm the room, usual throwaway niceties. It's just her way.'"

There's no doubt Wintour's success is due in large part to hard work, but you can't deny the natural talent aspect of it as well. As Wintour herself explained to New York magazine, "learning how to be editor-in-chief of Vogue wasn't something that happened overnight." Wintour's childhood was heavily influenced by the media. "My dad was a newspaper editor. My mother was a film critic, and my brother is the political editor of the Guardian," she told New York. Wintour attributes her interest in journalism and the media to her father. "I think the fact that he was so well known may be why I chose to go into magazines and move to the States at a young age," she said in an interview with Teen Vogue.

Aretha Franklin, Quentin Tarantino, and Anna Wintour. What do they all have in common? Well, for one, they're all super successful. For two: they all dropped out of high school. According to Wintour's Biography profile, she dropped out of school and got her first job as a teen. "I wasn't academically successful," Wintour said in a CBS News interview. "And maybe I've spent a lot of my career trying to make up for that," she mused. At this point, it's safe to say she's done that and more.

You don't get to be the editor-in-chief of Vogue without stepping on a few toes. Even as a young aspiring editor, Wintour wasn't afraid to speak her mind and make herself known. According to New York magazine, when Wintour first interviewed for a job at Vogue she told then editor-in-chief Grace Mirabella that she was coming for her job. Unfortunately for Mirabella, Wintour's comment came true. In her book In And Out Of Vogue, Mirabella revealed that Wintour often went behind her back to get things done. "She'd go behind my back and redo layouts, bring in new art, circumvent me and my fashion editors," she wrote. "When she couldn't bypass my editors, she'd harass and criticize them." In a Vogue interview, Wintour credited such perseverance to her father.

Wintour's icy demeanor and cunning attitude towards work didn't go unnoticed. So when the book and subsequent feature film The Devil Wears Prada were released in the early 2000s, many speculated that Meryl Streep's character Miranda Priestly was based on Wintour. Written by Lauren Weisberger, a former Vogue employee, The Devil Wears Prada depicted Streep's character as incredibly hard to please (and scary, even).

But should we assume Miranda Priestly is an accurate depiction of Wintour? "It wasn't a one-to-one portrayal," Weisberger told Daily Mail Online. "But of course my time at Vogue informed the book, there's no denying that." Of course, Wintour's seen the film. So what does she think about it? "I thought the film was really entertaining," Wintour told Barbara Walters in 2006. When asked if she recognized herself in Streep's character, Wintour said, "if Meryl seemed somewhat strong, I respect that."

In between all of her fashion show appearances, Met Galas, and Vogue issues, Wintour somehow made time to have a family. She has a son, Charles Shaffer (who welcomed a daughter to his family in 2017), and daughter, Bee Shaffer. Wintour admitted to New York magazine that balancing a family and her career wasn't always easy, and says she often tried to combine the two worlds. "Of course there were times, particularly when you travel, when it's very tough to leave the kids, particularly when they were very young," she said. "I would try to take them with me when I could just so they could experience and see a little bit of what a workday involved."

Originally married to psychiatrist David Shaffer, Wintour eventually cheated on him with businessman Shelby Bryan. According to a New York magazine feature, the two (both married) met in 1997 and carried on an affair that eventually led to the end of both of their marriages. As a shy, private person, you can probably imagine how tough the tabloid coverage and public scrutiny were for Wintour. However, she tried to ignore it as best she could. "You know that your friends and your family have one vision," she told New York, "and if the outside world has another, then that's just something that you just don't focus on."

Despite constantly being in the public eye, Wintour deeply values her privacy. For that reason, she avoids using social media. She doesn't have an official Instagram or Twitter, and didn't even appear on the Vogue Instagram page for the first time until 2013. "Social media has changed the way we look at everything, and I think it's amazing and incredible and fascinating," she told New York. "I follow my daughter. I follow Mario Testino. But it's not something I choose to do for myself." But wait: it gets crazier. The fashion mogul told Vogue that she still has a flip phone, and has never taken a selfie — what!?

The former First Lady's fashion influence during her time in the White House is obvious. In fact, her fashion choices were even the subject of a Harvard study. And of course, no fashion influencer can escape Wintour's radar — so it's no wonder the two women became close. Michelle Obama scored three Vogue covers throughout her eight years as First Lady, and was the one to cut the ribbon during the unveiling of the Met Museum's unveiling of the Anna Wintour Costume Center in 2014.

If you ever find yourself in the position of meeting the honorable Anna Wintour, remember this: don't wear all black! In her memoir Tales From The Back Row, Amy Odell reveals that a former Vogue employee warned her not to wear black to her interview with the Vogue editor-in-chief. Her warning certainly has merit. In a Vogue interview, Wintour herself told model Karlie Kloss that she would never be caught wearing "head-to-toe black."

Fashion is undoubtedly Wintour's true passion, but she also loves tennis. She told Vogue she plays the sport as often as she can (her dream teammate would be either Roger Federer or Serena Williams, naturally), and if there was one thing she could make a documentary about it'd be tennis.

Other than tennis knowledge, if you ever need to impress Wintour just talk about museums. When Teen Vogue asked Wintour what a potential Vogue employee should know, Wintour responded, "do your homework, go online, visit every museum, and intern." Journalist Amy Odell learned this firsthand during an interview with Wintour for a position at Vogue. In her memoir Tales From The Back Row, Odell detailed how Wintour and her associates continuously asked about Odell's museum knowledge and preferences. Wondering which museum you should visit first? Try the Metropolitan Museum in New York City, where Wintour has a costume center named after her.

Wintour is well-known for her unofficial uniform: a short bob with bangs that sweep the dark sunglasses that rarely leave her face. In an interview with Barbara Walters, Wintour revealed that she's had the same haircut since she was 15 years old. "I'm sure it's very boring and I should change," Wintour told Walters. "But every time I've tried it hasn't worked." And her sunglasses? Wintour told CBS News she considers them her armor. "I can sit in a show, and if I'm bored out of my mind, nobody will notice," she explained. "And if I'm enjoying it, nobody will notice. So, I think at this point they've become, you know, really armor."