Her first Vogue cover broke the norm - It featured Israeli model Michaela Bercu in a Christian Lacroix Haute Couture top and jeans. Wintour said that the top was part of a suit but that the bottom didn’t fit Bercu. As Wintour put it, “It only served to reinforce the idea to take couture's haughty grandeur and playfully throw it headlong into real life and see what happened."

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Print journalism is in her blood - Her father Charles was the editor of the London Evening Standard from 1959 to 1976. He also consulted with her on how to make the newspaper relevant to young readers.

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She has three siblings - Patrick, James, and Nora. Her oldest brother, Gerald, died in a car crash as a child. Patrick Wintour is the diplomatic editor of The Guardian.

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Her thoughts on New York - Wintour once told The Telegraph that she loves New York because it "is a city for people who want to work. And I love that it is a city where everyone is from somewhere else - so you are not judged by your accent, who your dad was, or any of that Englishness."

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The Met Gala - Wintour has presided over the Met Gala, AKA the most wonderful time of the year for A-listers around the world, since 1995!

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The Met Gala - She has the final say over every single person who attends. So, no, your invitation was not lost in the mail.

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One of the highest fashion honors - The Metropolitan Museum of Art in New York named its Costume Institute after her in 2014. After helping to raise $125 million for the wing, the institute was renamed The Anna Wintour Costume Center.

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One of the highest pop culture honors - Rihanna, unofficial queen of the Met Gala, tweeted that Anna Wintour was the best dressed at the 2019 event.

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Assistants - Wintour reportedly has three full-time assistants, but sometimes surprises callers by answering the phone herself.

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The Dame is punctual - She’s often early, in fact, and she can often be found alone on front rows at catwalk shows, waiting for the action to start.

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The immaculate bob cut - Another Anna Wintour staple is her severe bob haircut, which she reportedly maintains with two blow-dries a day: one first thing in the morning, and one early in the evening.

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The immaculate bob cut - If you can't picture her without it, that's probably because she started wearing the iconic bob as a young teenager.

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Early dating - At the age of 15, Anna started dating a well-connected older man, the then-24-year-old Piers Paul Read.

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Her first marriage - In 1984, Wintour married her first husband, psychiatrist David Shaffer.

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For the love of Chanel - When starting out at Vogue, Wintour only wore Chanel skirt suits. She reportedly continued to wear them during both her pregnancies.

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First child - Wintour and Shaffer's first child Charles (Charlie) was born in 1985.

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Second child - In 1987, Wintour and Shaffer welcomed their second child, Katherine (known as Bee). According to Bee, her mother is "the most generous person you will ever meet and she puts everyone else before her."

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Fashion in the family - Bee is now married to Francesco Carrozzini, the son of late Vogue Italia editor Franca Sozzani. Amidst all the fashion excitement, Bee has also described her mother as someone who "gets bored easily," but you must admit she keeps things trendy in snakeskin!

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She’s currently married - Wintour and Shaffer divorced in 1999, and in 2004 she married Texan venture capitalist Shelby Bryan.

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A 20-year love affair - With the same style of Manolo Blahnik shoes! The cross-front slingbacks feature a delicate kitten-heel and never veer too far from Wintour's skin tone (she is rumored to have different shades to accommodate for a tan).

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She's a loud and proud democrat - Wintour teamed up with Calvin Klein and Harvey Weinstein to raise funds for Barack Obama's presidential campaign.

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And she’s a big fan of Michelle Obama - Wintour loves the democratization and increased accessibility of fashion today, and she believes Michelle Obama was key in that process by changing the First Lady uniform. “She has changed the way American women see fashion."

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She was there for Hillary Clinton - She also supported Hillary Clinton's 2016 presidential campaign.

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They go way back - They go way back, as do Wintour's left-wing beliefs.

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Fundraising for AIDS - Since 1990, she has raised over US$10 million for AIDS charities.

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The morning routine you'd expect - Wintour claims that every morning she is up at 5 am. She plays tennis, has her hair and makeup done, and gets to Vogue's office to start the work day.

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She’s a big tennis fan - Wintour is a regular not only at fashion shows, but also at the US Open, Wimbledon Championships, and French Open tournaments.

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A soft spot for Federer - She is very good friends with Swiss tennis player Roger Federer. She has attended some of his matches, and his victory over Andy Roddick at Wimbledon is said to be her all-time favorite match.

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A rare party animal - According to the BBC documentary 'Boss Women,' Anna rarely stays at parties for more than 20 minutes, and gets to bed by 10:15 pm every night.

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Want her to hire you? - She likes strong personalities. "I don't like people who'll say yes to everything I might bring up. I want people who can argue, and disagree, and have a point of view that's reflected in the magazine,” she told The Telegraph.

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Unplugging - Wintour also turns off her cell-phone during lunchtime in order not to be disturbed.

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High-protein meals - For a long time, high-protein meals have been a habit for Wintour, usually eating a steak or a bun-less hamburger. In 'The Devil Wears Prada,' protagonist Miranda Priestly (a thinly veiled Wintour) eats a freshly cooked steak from a top restaurant for lunch in her office every day.

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'The Devil Wears Prada' - In 2003, Wintour's former assistant Lauren Weisberger wrote a novel loosely based on Wintour. It was later made into a movie, starring Meryl Streep as a merciless fashion editor.

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Prada premiere - When attending the premiere of the movie, the real-life editor humored everyone and showed up wearing Prada.

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Streep says she was not the focus - "I wasn't at all doing some sort of thing on Anna Wintour," she told IndieWire in 2016.

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A little sting - Wintour was said to have been more hurt by her former assistant's novel than the film adaptation.

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Prada power lunch - Early in May 2019, Wintour was spotted giving Streep an affectionate cheek kiss during the pair's hour-long power lunch in Manhattan, 13 years after the film was released.

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The September Issue - In 2009, she was yet again the focus of a movie, this time R.J. Cutler's documentary 'The September Issue.'

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The occupational hazard of loving fur - In October 2005 she was the unexpected recipient of a pie-in-the-face on behalf of PETA (People for the Ethical Treatment of Animals) on the way to a Chloé show during Paris Fashion Week. protesting against the promotion of fur in the magazine.

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Her one absolute fashion no-no? - You'll never see her in head-to-toe black.

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Her favorite literary fashion icon - Wintour lists 'Gone With the Wind' protagonist Scarlett O'Hara as the most fashionable literary figure.

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'Game of Thrones' fan - Wintour is a reportedly a big fan of the TV show, particularly for the costume design, of course.

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Recycling looks - Wintour is not too posh to recycle her outfit, and she's often been spotted in the same Prada dresses and colored crystal necklaces.

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Retirement in sight? -

Most 69-year-olds are already in retirement, but in 2013, Wintour took on even more work and became artistic director for Condé Nast, Vogue's publisher, and in July 2014 became editorial director.

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"Nuclear Wintour" - Her alleged frosty demeanor has earned her the nickname of Nuclear Wintour, but at the end of this gallery you might have a different opinion.

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The big sunglasses - The front-seat staple explained that she wears those sunglasses because they hide her thoughts, particularly her boredom, plus they cover her tired eyes.

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What can convince her to take them off? - Certainly not the Oscars, as she didn’t once remove her glasses at the 2015 ceremony, but she did ditch the shades when she was made a Dame in 2017.

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Before Vogue - Wintour started her career at Harpers and Queen (now Harper's Bazaar) in London, and worked for a time at Harper's Bazaar US, British Vogue, and House and Garden magazine.

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Vogue in New York - The British-American journalist has most famously been editor-in-chief of American Vogue since 1988.

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