The Fabulous Life of Anna Wintour

Anna Wintour has remained one of the fashion world’s top dogs for decades. The editor-in-chief of Vogue may be known for her cut-throat attitude and incredible style, but her past is almost as colorful as her dresses. Join us as we take a look at the fabulous life of Anna Wintour, from her English roots to her glamorous New York lifestyle. You might be just as surprised by her morning routine as we were!

Made in the UK

Anna and her dad
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Anna Wintour was born in London in 1949 to the editor of Evening Standard, Charles Wintour and his American wife, Eleanor Trego. Journalism is in her blood – so much so that when her parents divorced in 1979, her father married Audrey Slaughter, the editor of Honey and Petticoat.

18th Century novelist Lady Elizabeth Foster, Duchess of Devonshire, was Wintour’s great-great-great-grandmother, and Sir Augustus Vere Foster was a granduncle. You could say that Anna was destined for her famous role as Editor-in-Chief of US Vogue, but it wasn’t just her bloodline that preempted her career. Anna grew up in the swinging ’60s, and she couldn’t get enough of fashion.

She’s Had Her Famous Hairstyle Since She Was 14

Anna in the 60s
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At school, Anna would frequently rebel against the strict dress code by taking the hem up on her skirts, and by the age of 14, she had cut her hair into a very of-the-moment bob style she remains famous for. The youngster adored watching popular music shows like Ready Steady Go! and devoured the copies of Seventeen that her grandmother sent her from the US.

Her father, often in need of a young persons’ perspective for his work, would consult her frequently on different subjects in order to appeal to the youth. “Growing up in London in the ’60s, you’d have to have had Irving Penn’s sack over your head to not know something extraordinary was happening in fashion,” Anna later recalled.

From Fashion Classes to Journalism

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Her father was keen for his daughter to pursue a career in the fashion industry, arranging for Anna to work at the popular Biba boutique when she was 15. After a while, Anna moved on to take fashion classes. Surprisingly, she soon dropped out, realizing that designing wasn’t for her. "You either know fashion or you don’t," she would later state.

Not long after, Anna landed a job as an editorial assistant at Harper’s Bazaar, thus kickstarting her career in fashion journalism. From that point on, she had her sights set on Vogue, telling her colleagues that she would be the editor one day.

Rivalry Forced Her to Move Stateside

Anna at Harpers
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Although Anna was doing well at Harper’s Bazaar UK, she constantly butted heads with the editor, Min Hogg. The pair frequently disagreed about everything from photo placement to what models to pick. With work life now intolerable, Anna made the decision to move to New York with her journalist boyfriend, Jon Bradshaw.

Her rivalry with Hogg didn’t stop her from landing a job as a junior fashion editor with the US version of the magazine in 1975, but editor Tony Mazzola didn’t like her style, which pushed the boundaries of what he deemed acceptable. Wintour was fired after nine months.

Scandalous Connections

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Bradshaw quickly began scouting around for potential jobs for his unemployed beau, using his connections to secure her a position at Viva, a women’s adult magazine. Kathy Keeton, the wife of Penthouse publisher Bob Guccione was the proprietor. The content was raunchy and largely focused on sex. Anna declines to talk about that period of her life in interviews.

Despite the unsavory publication, Anna was treated well at her new position, which had enough room in the budget for her to hire a personal assistant. This would be the beginning of her reputation as "Nuclear Wintour", the demanding and formidable boss. It’s a name she would never escape.

Meryl Streep’s Character in The Devil Wears Prada is Based on Her

Anna and Meryl
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Former assistants to Wintour all make it clear that Anna likes everything just so. When it comes to interviewing for her, potential employees have spent a month’s salary on a brand new current season outfit just to impress.

It’s reported that the hit movie The Devil Wears Prada was partially based on the author’s experience as Anna’s assistant. Meryl Streep plays the domineering boss that is vicious, headstrong and incredibly well respected in the industry. Lauren Weisberger has never confirmed that the character is based on her former employer, but it doesn’t take a genius to put two and two together.

Her Love Life is as Colorful as her Fashion Sense

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Anna started dating influential men early on in life, often embarking on relationships with older gentleman. Psychiatrist David Shaffer captured her heart in the ’80s, and the two went on to marry and have a son, Charles, and a daughter, Katherine (known as Bee). The union lasted for over 15 years until Wintour’s head was turned by investor Shelby Bryan.

Bryan was also married when the pair met at an NYC benefit, but the chemistry was undeniable. An affair ensued, and both parties ended their relationships in 1999 so they could be together. They continue to be committed to each other, although they have never tied the knot.

Enemies in High Places

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By the early ’80s, Anna had made a name for herself in the industry as an exciting and innovative editor. When Viva dissolved, she went on to work as fashion editor at Savvy, and then New York. By this point, she was experienced, but working at New York taught Anna a valuable lesson – celebrities sell copies.

Through a colleague, the talented go-getter landed an interview at Vogue – but it didn’t quite go to plan. Grace Mirabella (pictured) had been the editor of the magazine since 1971, so when Anna walked in and proudly proclaimed that she wanted her job, it went down like a lead balloon. Mirabella didn’t want her on board, but luckily for Wintour, she had another precious connection.

From "There’s the Door" to Bidding War

Anna 1989
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Although Vogue had always been Anna’s dream, she knew how to play hard ball. When editorial director for Conde Nast, Alex Liberman, approached her about working for the magazine, Wintour held back. A bidding war ensued, and Anna signed a deal for double her current salary.

Wintour wasn’t about to nestle in quietly as the creative director either. Mirabella’s ideas were often undermined and changed at the last second at Anna’s bequest, causing friction between the staff. After a while, she assumed complete control of the UK version of the magazine – her first full editorship. Anna ripped through the place like a bull in a china shop.

"The Wintour of our Discontent"

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Now able to do what she wished at Vogue UK, Anna wasted no time in putting her stamp on the place. She fired many of the staff and insisted on overseeing processes never before done by a previous editor.

Gone were the days that Vogue UK had known previously as it was shunted in the direction of its American counterpart. "There’s a new kind of woman out there," Anna told the Evening Standard. "She’s interested in business and money." While some employees praised her cut-throat attitude, others that survived the mass cull called the transitional period "The Wintour of Our Discontent."

There’s a Reason for the Sunglasses

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Anna Wintour is as famous for her personal style as she is for her incredible work ethic. However, one thing has baffled celebrities and readers alike – Anna’s penchant for wearing sunglasses indoors. Wintour rarely takes them off, even when she sits in the front row of a fashion show next to the Queen.

In 2009, she explained her sunglass strategy goes way beyond fashion. "They are seriously useful," she told 60 Minutes. "If I am bored out of my mind, nobody will notice. At this point, they have become, really, my armor." And of course, they are always Chanel.

Anna Has Unlikely BFF’s

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Let’s face it, being the editor-in-chief of Vogue has its perks. Not only do you get a killer wardrobe, but you rub shoulders with all of the A-listers, and in some cases, royalty…however, Anna has managed to forge some unlikely friendships.

British TV presenter James Corden caught the media mogul’s eye when he was performing the lead in the West End play One Man, Two Guvnors back in 2011. Anna reached out to the star, sending him a card that read, "To James, from your biggest fan and most avid stalker, Anna." In fact, it was Wintour that got Corden the gig on The Late Late Show by meeting with the president of CBS.

Vogue Gives Her $200k A Year For Clothes Alone

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Anna already gets paid a pretty penny to run the show at Vogue, but she also gets an incredible allowance for her clothing. As one of the most influential fashion icons in the world, it’s probably a wise investment by Conde Nast… even if it costs them an additional $200k a year.

She may have flunked out of fashion school, but Anna knows the latest trends like the back of her hand – and won’t be caught in the same thing twice if she can help it. We’d love to take a peek inside of her closet – it’s probably worth millions.

Not Everything Went to Plan

Anna Wintour
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After working successfully for British Vogue, Anna accepted a position in New York at the helm of another Conde Nast publication, House & Garden in 1987. Bosses hoped she would work her magic on the magazine, which was in stiff competition with Architectural Digest. Unfortunately, it didn’t go to plan.

Wintour took the lifestyle magazine in a new direction, renaming it HG and injecting fashion articles where DIY tips had previously been. Subscribers began dropping like flies, with most of the long-running advertisers pulling out, too. Ten months later and Wintour got the job she had once told Grace Mirabella she wanted – editor of US Vogue.

The Winning Combination

First Vogue
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By this point in her career, Anna had been around the block enough to know what works and what didn’t – but she also wasn’t scared to try new things. On her first edition of the magazine, she ditched the up-close headshots and instead used a casual, full-body shot of a model wearing jeans. It was a sensation.

Some editors left to work at competitors, leaving Anna to form a new core staff. In the 2000s, Anna was bestowed with praise for her work, even receiving an OBE from the Queen in 2008, but it wasn’t all plain sailing. 2008 would be bittersweet for the editor-in-chief.

"The Worst Fashion Faux Pas of 2008."

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It’s usually Anna that does the appraisals of outfits, so when critics called her 2008 Met Gala gown "The worst fashion faux pas" of the year, Wintour was less than thrilled. Her bad luck didn’t end there. The newly launched Men’s Vogue cut back to two issues a year as an outsert to the women’s magazine. Vogue Living was shelved completely, and December’s cover featured Jennifer Aniston criticizing Angelina Jolie.

Some in the industry called the magazine "stale and predictable", with others saying that Wintour had lost her touch. Rumors began to swirl that Conde Nast would replace her with the Russian Vogue editor, but Anna wasn’t going anywhere. She was just getting started.

Conde Nast’s Artistic Director

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Spurred on by some tough times and the portrayal of herself in The Devil Wears Prada, Anna started to appear in more interviews, which helped to soften her image. By 2013, it was clear Wintour wasn’t going anywhere as Conde Nast gave her the role of artistic director for all of their publications, while still remaining at Vogue.

In 2014, she was named the 39th most influential woman in the world by Forbes. Journalist Alison Herman said, “Wintour isn’t just redeemed. She’s openly admired, Arctic chill and all.” To this day, Wintour remains one of the best in the business – if not the best.

Her Morning Routine is as Sharp as Her

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Like many successful people, Anna gets up earlier than most. By 5:45 am, she’s at New York’s Midtown Tennis Club, racket in hand and ready to play an hour of the sport. After that, she has her hair and make-up professionally done before heading into her office at One World Trade Center.

Her morning consists of meeting after meeting, but these aren’t long-haul slots. Each consult lasts around five minutes, with anything over seven minutes considered long. Her time is so precious that even her long-suffering assistants are lucky to get it.

She Adores Manolo Blahnik

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Anna loves to keep up with current trends – it is her job after all – but she also knows the value of a classic. Wintour has been rocking the same style of shoe for over twenty years.

Her obsession with designer Manolo Blahnik started in 1984 when she began wearing nude sandals to events. These days, the star wears the exact same style to pretty much every single red carpet event and Met Gala ball that she attends – and that’s a lot. The low-heeled slingback sandals were designed for Anna by Blahnik himself. Who wouldn’t want bespoke shoes made by the famed brand?

Her Daughter is her Date

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Although Anna is in a loving relationship with her partner, you can always find her walking the red carpet alongside her daughter, Bee Shaffer. The pair often attend events together, when Shaffer can take a break from her own hectic schedule to see her mom.

The brunette beauty previously worked as a producer on Late Night with Seth Meyers, before moving on to partner up with the Ambassador Theatre Group. The mother-daughter combo always supports one another in their endeavors and are a tight (and incredibly stylish) unit. Shaffer tied the knot with film director Francesco Carrozzini last year.