I’m dying to know who started the rumor about Anna Wintour and Bob Marley having an affair.
Anna: The Biography, fashion journalist Amy Odell’s new, unauthorized book about the notoriously private Anna Wintour, came out last week, and it’s full of incredible secrets and stories about Wintour’s life and career.
While Wintour declined to be interviewed for the book, over 200 of her friends, fellow fashion insiders, and former employees spoke to Odell about what it was like to work for the legendary Vogue editor.
Here are 17 beyond fascinating details that I learned from reading Anna, from her very specific food preferences, to her rumored affair with Bob Marley:
When Anna was an editor at New York magazine, she was caught throwing pennies away in the garbage can at her desk. Some staff members allegedly raided her trash after she left work every night to scoop up the coins.
After going to a Bob Marley concert with her then-husband David Shaffer, a rumor that Anna disappeared and had a two-week affair with Marley began flying. While it’s unclear exactly how the rumor got started, she reportedly told staffers that the concert had been a “life-changing experience.”
Many believed Anna was angling to become an ambassador to the United Kingdom had Hillary Clinton won the 2016 election. Anna and Hillary actually go way back. In 1998, Hillary Clinton was the first First Lady to ever be on the cover of Vogue. The story was actually supposed to be just a feature inside the magazine, but after the story of Bill Clinton’s involvement with White House intern Monica Lewinsky broke, Anna decided Hillary should be on the cover.
When Condé Nast, Vogue’s parent company, moved their headquarters from Times Square to 1 World Trade Center, Anna began frequenting The Palm, a nearby restaurant. She ordered the same thing for lunch every day: a steak and a Caprese salad with no tomatoes, which is essentially just a pile of cheese drizzled with olive oil. According to Grub Street, the meal, with tip, costs $73.33.
Anna is as particular about the food for the Met Gala as she is her lunch. She has banned chives, garlic, onions, and parsley from the event because it would get stuck in people’s teeth and make their breath smell. She also refuses to serve fish because she doesn’t like the way it smells. So what does Anna like? Her go-to meal to serve at events is chicken pot pie, because it’s “a one-course meal that has everything.”
Before Anna got her gig at Vogue, she proposed a story idea that she had been working on for months to Interview, the magazine owned by Andy Warhol. When her idea was rejected, Anna reportedly started crying, something Warhol said he had never imagined seeing. About a month later, Warhol and Anna ran into each other at a restaurant. “Maybe we should have hired her,” he wrote in his diary. “We do need a fashion person, but I don’t think she knows how to dress. She’s actually a terrible dresser.”
Fashion Week is obviously a big deal for Anna. After the birth of her first child, people began speculating that she had begged doctors to induce her early so that she would be able to attend the couture shows. Anna’s brother Patrick later said that the story was a “fabrication.”
Anna had a hard time fitting in at New York magazine, as a glamorous fashion editor among journalists. Several staff members tried to play a well-intentioned joke on Anna, and got everyone on staff to put their hair up in a little bun on top of their heads, which is what Anna did when she was concentrating. Once Anna got the joke, she reportedly burst into tears and ran out of the room.
Being Anna’s assistant was pretty much exactly like how it was portrayed in The Devil Wears Prada. She has three assistants at any given time: the first is her primary assistant, the second takes care of her home and dogs (at one point, she had golden doodles who were all named after characters from To Kill a Mockingbird), and the third is in charge of running errands and organizing Anna’s clothes. One assistant said they were terrified to ride in the elevator with her because Anna would list off everything they needed to do, even though they weren’t by their desks to write her demands down. They also were scared to leave their desks to go to the bathroom. Anna would typically address all of the assistants using the first assistant’s name, until she was sure they were going to last at Vogue.
Speaking of The Devil Wears Prada, the book was written by Lauren Weisberger, who was one of Anna’s assistants in the early 2000s. When the novel was announced, Anna reportedly said, “I cannot remember who that girl is.” When the book came out, Weisberger repeatedly denied that Miranda Priestly was based on Anna. After reading the book, Anna reportedly was “bemused” by it, but said she found it difficult to read.
When The Devil Wears Prada hit theaters, Anna saw the film at a special, invite-only screening. She showed up to the event wearing a Prada dress. After finishing the movie, Anna’s daughter turned to her and said, “Mom, they really nailed you.” Anna left as the credits started so she could avoid running into anyone who might be wondering exactly how accurate Meryl Streep’s portrayal was.
According to Miranda Brooks, Anna’s garden designer, Anna refused to plant a vegetable garden at her Mastic, Long Island compound because she said she “didn’t like vegetables.” Despite the lack of a vegetable garden, Anna’s estate has two swimming pools, an upper and lower house, barns that have been converted into guest cottages, and a “bistro barn” for dinner parties. Guests at Anna’s dinner parties often have to play games where they answer trivia questions. If they get the answer wrong, they must dump a glass of ice-cold water on their heads. Don’t worry, guests have said that Anna’s a good sport who plays by the rules when she gets a question wrong.
Anna put Madonna on the May 1989 cover of Vogue after a man on a plane told her that Vogue was “very classic and beautiful. It’s Katharine Hepburn; it’s Audrey Hepburn; it’s Grace Kelly — it would never be Madonna.” Anna took his comments as a challenge, and photographed the singer in a pool for the cover. When the issue came out, it sold 200,000 more copies than the previous year’s May issue.
Although the Kardashians are now Met Gala staples, Anna refused to let them attend for years. “The Kardashians had zero style, and their whole reason for who they were was nothing that tied to Vogue,” Stephanie Winston Wolkoff, Vogue’s events planner said. Apparently Anna thought that they were not people who could “make a difference” in the industry. She changed her tune in 2013, when Kim made her Met Gala debut. Others who Anna didn’t want at the gala included Paris and Nicky Hilton (who have still never attended), and Nicole Richie.
When Alexis Ohanian proposed to Serena Williams, he made sure to call Anna, who is close friends with Serena, for advice on the engagement ring. “From the second I got engaged, I barely said yes before I was calling Anna,” Williams said. Williams even called Anna, who is an avid tennis player, for advice when Williams felt like she was floundering in her tennis career.
In 2018, Vogue created a web series called Go Ask Anna, during which random people on the street could ask questions of the editor, who would answer them from her desk. Vogue saw the potential for sponsorships, and approached Anna about having chocolate on her desk in one of the videos. She said she would only appear with Ferrero Rocher or Lindt chocolate, and completely refused to be filmed with dark chocolate.
And finally, despite being an avid theatergoer, Anna reportedly gets bored during plays. If she begins crossing and re-crossing her legs, it means that she’d like to leave. She’s been known to leave Broadway shows less than an hour after they start.