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 promptly adapted into a 2006 big-screen blockbuster — made the editor an even bigger global icon.
And just in time for the sequel, the Vogue boss is getting in on the fun, having posed for the cover of her own glossy alongside Meryl Streep, who plays her onscreen alter ego, Miranda Priestly.
Vogue is leaning all the way into the “Devil” drama, with new head of editorial content Chloe Malle interviewing three former Wintour assistants on the brand’s “The Run-Through With Vogue” podcast this week.
Speaking with Sache Taylor, Sammi Tapper and Marley Marius — who all worked in “Anna’s office” for between one and four years, spanning from 2017 to October 2025 — Malle asked the trio to compare their real-life experience with the book and film.
Below, some of the biggest revelations from the chat.
The interview process
What to wear when you’re campaigning to be one of two (or, in more lucrative times, three) assistants to the EIC of all EICs? One surprising edict: no black. Wintour notoriously loves color, and once said the one thing she would never wear is head-to-toe black.
Also, don’t expect Wintour to inquire about strengths and weaknesses. Instead, “questions were personal,” recalled Tapper and Taylor.
“She doesn’t want a robot,” Marius said of the pre-interview advice she received from chief content operations officer Christiane Mack. “She wants someone with a personality.”
The daily routine
“I had a 21-page handbook,” said Marius of a seemingly sacred text passed down from assistant to assistant.
The day starts “really early,” Marius said, though she didn’t pinpoint a time. In her MasterClass, however, Wintour revealed she wakes up between 4 and 5:30 a.m. on workdays.
After reading the news (online at home these days rather than in print at her desk, as in “The Devil Wears Prada”) and playing tennis, she typically arrives in the office around 8 a.m. — where Marius said an assistant sets up her coffee and breakfast, opening the office doors and readying her schedule for the day.
Tapper confirmed Wintour is the first person in the office (besides her own assistants) each day.
While her “board” (her list of daily tasks and reminders) is set up on an iPad, Wintour’s schedule and most documents — including every email and response — are printed out for her review.
The “Clackers”
Marius copped to changing out of her “clogs” into “more appropriate shoes” once Wintour’s driver gave them the heads up that she’d arrived at Vogue HQ.
She recalled Wintour’s then-first assistant telling her “everyone in Anna’s office wears heels,” but Marius said she only lasted two weeks before she switched to flats.
“Things are happening at a certain pace and it sometimes involves a bit of running,” she explained. “So I was finding it not practical to be in heels.”
Why the need for speed? “When she asks for someone, she wants that person very quickly.”
Taylor, who was an assistant for four years beginning in 2019 and now plans the Met Gala as Vogue’s special events director, recalled “herding” sluggish editors into meetings with Wintour. There was a process: The first assistant would call those staffers on their landline desk phones, while the second assistant would race to their desks and ensure they moved swiftly.
“I would just hover until they were ready — if I hover, usually they were faster,” she said.
“I loved the running around because I was so busy that I could never exercise. So I would just run in the office.”
Take-home work
Anna is working around the clock. When she’s done with her day in office, the editor lugs her “take-home bag”: an extra-large L.L.Bean Boat and Tote filled to the brim with articles awaiting her edits, approval and notes.
“This is Anna’s homework bag,” Tapper explained. “She never wants anyone waiting on her for feedback.”
Malle agreed: “If three 4,000-word pieces come in in one night, she’s giving very detailed feedback on all of them by the next morning.”
The infamous “book” — which is featured heavily in “The Devil Wears Prada” and described as a “dummy book” of the magazine that’s set to go to print three to four months later — goes into the bag every night.
Winter then marks up the book with Post-It notes featuring her “doctors handwriting” that “takes a village” to decode.
“I would allow myself to ask her once a week [what one of her notes said],” Taylor recalled.
The dress code
While heels are encouraged, there’s no reason to make every day a runway. Taylor says she wore heeled Joseph boots with black trousers and a “different sweater every day” for a neat uniform that she’s carried through to her current position.
Marius favored collarless linen shirts and black pants with smoking slippers (after giving up on heels after two weeks). “You don’t want to wake up and have to think about what you’re wearing every day when you have to wake up so early,” she said.
Taylor recalled other assistants of Wintour’s who had on “a full outfit every day,” saying, “I just didn’t understand how they did that.”
Tapper spent several weeks wearing pumps that gave her “crazy blisters” before “retiring” them — but still always wore some type of heeled shoe to the office except on Fridays, when she might opt for a ballet flat “if [her] feet were getting tired.”
“While at Vogue, you never know what’s gonna happen,” Tapper said of her suited-up style. “So you have these important meetings with these important people pop up … Anna has people meeting her and she’ll pull you into meetings, so it’s always nice to have at least a little blazer.”
The one “unspoken rule” of those working closest to Wintour, according to Tapper? No jeans and no sneakers.
As for borrowing from the illustrious fashion closet, like Anne Hathaway’s character in the film? Definitely more fiction than fact — with exceptions, of course.
