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Sometimes truth is stranger than fiction.
Anna Wintour’s reputation has always preceded her, and the release of Lauren Weisberger’s 2003 novel The Devil Wears Prada (which was quickly adapted into a big screen movie in 2006) made the editor an even bigger global icon.
And just in time for the sequel’s release, the Vogue boss is getting in on the fun by gracing the cover of her own glossy alongside Meryl Streep, who plays her on-screen alter ego Miranda Priestly.
Vogue is fully committed to the “Devil” drama, with new head of editorial content Chloe Malle interviewing three former Winter Tour assistants this week on the brand’s podcast, “The Runthrough with Vogue.”
Maru spoke to Sachet Taylor, Sammy Tapper and Marley Marius, who worked at Anna’s Office for one to four years from 2017 to October 2025, and asked them to compare their real-life experiences to the books and movies.
Below are some of the biggest takeaways from our chat.
interview process
Of all the EICs, what should you wear when you’re campaigning to become one of the EIC’s two (or more advantageously, three) assistants?There’s one surprising edict. It’s about banning black people. Wintour is famous for her love of color, and has said that the only outfit she would never wear was head-to-toe black.
Also, don’t expect Winter to ask you about the pros and cons. Rather, “the questions were personal,” Tapper and Taylor recalled.
“She doesn’t want a robot,” Marius said of the advice she received before her interview from chief content operations officer Christiane Mack. “She wants someone with personality.”
daily routine
“I had a 21-page handbook,” Marius said of the seemingly sacred document that was passed down from assistant to assistant.
Marius said his day starts “really early,” but he did not specify the time. But Winter revealed during the master class that she wakes up between 4:30 and 5:30 a.m. on weekdays.
Marius said he usually arrives at the office around 8 a.m. after reading the news (these days, online at home, rather than reading it in print at his desk like The Devil Wears Prada) and playing tennis. There, an assistant prepares coffee and breakfast, opens the office door, and prepares the day’s schedule.
Ms. Tapper acknowledged that Ms. Winter is the first person (other than her own assistants) to come into the office each day.
Although her “board” (a list of daily tasks and reminders) is set up on an iPad, Winter’s schedule and most of her documents (including all emails and responses) are printed for review.
“cracker”
When Winter’s driver tells him that he has arrived at Vogue headquarters, Marius attempts to change from his “clogs” to “more appropriate shoes.”
Marius recalled that Winter’s first assistant at the time told her that “everyone in Anna’s office wears heels,” but they only lasted two weeks before switching to flats.
“Things are moving at a certain pace and sometimes you need to run a little bit,” she explained. “That’s why I didn’t think it was practical to wear heels.”
Why do we need speed? “When she wants someone, she wants him right away.”
Taylor, who worked as Vogue’s assistant for four years starting in 2019 and is currently planning the Met Gala as Vogue’s special events director, recalled “driving” out-of-work editors into meetings with Wintour. There was a process. The first assistant called the staff member on the landline, and the second assistant rushed to the desk to help the staff move quickly.
“I just hovered until they were ready. If I hovered, they were usually faster,” she said.
“I loved running around because I was too busy to exercise, so I just ran around the office.”
take-home work
Anna works around the clock. When she finishes her day at the office, the editor carries a “take-home bag.” It’s an oversized LLBean boat and tote filled to the brim with articles waiting to be edited, approved, and noted.
“This is Anna’s homework bag,” Tapper explained. “She never wants anyone to wait for feedback.”
Malle agrees. “If we receive three 4,000-word pieces in one night, we get very detailed feedback on all of them by the next morning.”
The infamous book, which was featured extensively in The Devil Wears Prada and is scheduled to be published in three to four months, is placed in the magazine’s bag every night.
Winter marks the book with post-its featuring her “doctor’s handwriting” that “takes a village” to decipher.
“I gave myself permission to ask her[what was written in her notes]once a week,” Taylor recalled.
dress code
Wearing heels is encouraged, but there’s no reason to make every day a runway. Taylor said he wears a formal uniform of heeled Joseph boots, black pants and a “different sweater every day,” which he said has carried over into his current position.
Marius preferred collarless linen shirts and black pants with smoking slippers (after giving up heels in two weeks). “You don’t want to have to wake up so early and then have to think about what you’re wearing every day,” she says.
Ms. Taylor recalled that Mr. Winter’s other assistants wore “dressed up every day,” and said she “couldn’t understand how anyone could do that.”
Tapper wore pumps for several weeks and developed “terrible blisters” before “retiring them,” but she said she always wore some type of heel to the office except on Fridays, when she would opt for ballet flats “if my feet got tired.”
“When you’re at Vogue, you never know what’s going to happen,” Tapper said of his suit-wearing style. “So suddenly you have an important meeting with important people…Anna has people who are meeting her and she pulls you into the meeting, so it’s always good to have at least a little blazer.”
According to Tapper, what is the one “unspoken rule” for those working closest to Winter? No jeans or sneakers.
As for borrowing from famous fashion closets, like Anne Hathaway’s character in the movie? Of course, there are exceptions, but they are more fiction than fact.
