When you hear the name “Anna Wintour,” what comes to mind? Some people immediately associate her with Miranda Priestly, the dragon lady of The Devil Wears Prada . In contrast, others think of her impenetrable look, including the chin-length bob and opaque sunglasses. Still others go straight to her career as editor-in-chief of Vogue .
Honestly, every one of these responses bears some truth. But these associations only tell a fraction of the story when it comes to this fascinating fashion figure. Not only is Wintour a spot-on style icon in her own right, but she’s maintained an incredibly low profile despite riding shotgun on the celebrity roller coaster for decades. Her magazine, American Vogue , reaches a jaw-dropping 12 million print readers and 1.2 million online visitors per month.
Here are some of the craziest things you never knew about Anna Wintour.
Anna Wintour wouldn’t have a career in style if it weren’t for her uncanny ability to keep her finger on fashion’s pulse. Think of her as the veritable Oracle of Delphi when it comes to the “in look.” Her insights have sometimes proven highly controversial, too. But that’s okay, because she doesn’t mind shaking things up. Take, for example, the first cover she ever dropped as American Vogue’s editor-in-chief.
Published in November 1988, it features pregnant model Michaela Bercu wearing a black mid-drift sweater featuring a gaudy jewel-encrusted crucifix applique, stone-washed Guess jeans, and the tiniest hint of a baby bump. She’s wearing very little makeup, has tendrils of hair blowing across her face, and is smiling so widely her eyes appear semi-closed.
This candid shot wouldn’t make anyone think twice today, but it sent shockwaves through the industry back in 1988. After all, Vogue covers of the day went heavy on the makeup, jewelry, and formality.
Vogue in 1988: before Anna Wintour vs Anna Wintour’s first cover in november. February 1988 (left) November 1988 (right) pic.twitter.com/LLCSOU2BOI
— The Artémis Magazine (@theartemismag) December 26, 2020
So stunned were the magazine’s printers that they called up and asked sternly, “Has there been a mistake?” Despite the explicit criticism, Wintour held her ground. In a recent issue of Vogue commemorating the magazine’s 120th anniversary, she explained, “I had just looked at that picture and sensed the winds of change.”
By age 15, Anna Wintour was rocking the iconic chin-length bob that she still sports today. And she created her own apartment within her family’s home by transforming the servant’s quarters into a living space. This provided her the necessary freedom to live independently by her mid-teens. Perhaps this also demonstrated a rebellious streak when it came to following arbitrary rules and the caprices of authority figures.
By 1966, at the age of 18, this “streak” emerged in full force in her dealings with a new headmistress at the North London Collegiate School. After learning that Wintour sported a hemline shorter than the school permitted, the headmistress decided to make an example of her and tore the hem of Wintour’s skirt as a punishment. This proved the final straw for Wintour, and she dropped out of school shortly thereafter.
Wintour has described this period of her life as a very shaky start to her career, per The Guardian . But she also attributes her rise through the ranks of the fashion world to her geographic location. “I now know that this would never have happened in the States, as one of the big differences between American and British journalism is the expectation of qualification.” (It also likely helped that her father, Charles Wintour, was the editor of the London Evening Standard .)
According to New York Magazine , Wintour reportedly received a salary of $2 million in 2011, and we can only imagine how much this has gone up over the past eleven years. What’s more, she’s now the Condé Nast artistic director, which likely came with a significant pay raise or two (via the Independent ). But that’s just one part of her well-paying job.
Wintour also receives a clothing allowance from Vogue that’s higher than her employees’ salaries and could put a significant dent in your mortgage. According to Business Insider , the Vogue editor-in-chief gets a massive $200,000 per year to stay impeccably trendy.
To give you a little perspective, consider the next highest-paid employee at Condé Nast: a creative director rakes in a measly $163,333 per year, as reported by Who What Wear . When it’s all said and done, Wintour is valued at $35 million.
In 2005, Jerry Oppenheimer wrote Wintour’s biography, including fun and surprising details about her private life. Titled Front Row: What Lies Beneath the Chic Exterior of Vogue’s Editor-in-Chief , the book claims to delve behind the cool-chic façade Wintour has cultivated over the years.
For example, Oppenheimer describes her enthusiastic adoration of Bob Marley, which motivated her to get a backstage pass to hang out with him and The Wailers night after night during the performers’ week-long stint in Manhattan while on tour.
According to sources close to Wintour, she treated Marley with a reverence bordering on blasphemy. “Anna met God . . . I don’t think anything moved her as much as Bob Marley.” Rumor has it she even hung out with Marley and his crew after shows.
That said, Wintour has never been a drinker, and she has also categorically stated that nothing romantic transpired between her and the iconic performer. So, the nights spent hanging out together proved relatively tame.
It seems Wintour did come away with some of Marley’s life philosophy. Despite her self-imposed cold veneer, which The Devil Wears Prada didn’t help, rumor has it she’s got a soft side. In an interview with Teen Vogue , her daughter Bee Shaffer said, “I know that she is the most generous person you will ever meet. It’s crazy. She puts everyone before her always.”
Between her daughter’s warm praises and the stories about Marley, Anna Wintour’s Ice Queen exterior quickly melts, and we’re left with a portrait of a deliciously complex female powerhouse who happens to wear Prada.
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