“The Devil Wears Prada Was True”: Anna Wintour’s Ex-Assistants Tell The Reality Of Working For The Vogue Icon

Anna Wintour has long been known for her strict reputation at Vogue, but fresh insights from her former assistants have offered a more detailed look at what the job actually involves.

Their accounts come as interest surrounding The Devil Wears Prada 2 has picked up ahead of its release on May 1, bringing renewed attention to Wintour’s professional life.

In the 2006 original film, Meryl Streep played Wintour’s alter ego, Miranda Priestly.

Anna Wintour’s former assistants revealed what it was really like working inside her office

Image credits: NBC

In an April 9 episode of The Run-Through With Vogue podcast, three of Wintour’s former assistants, Sache Taylor, Sammi Tapper, and Marley Marius, spoke about their time working directly under her between 2017 and 2025.

One of the first surprises came during the hiring process. Candidates were advised not to wear black, as Wintour is known to prefer color. Instead of typical interview questions, the process focused more on personality.

“She doesn’t want a robot… she wants someone with a personality,” Marius recalled being told before her interview.

Image credits: Getty/Jacopo Raule

Once hired, the job came with structure and intensity. Marius revealed she was given a 21-page handbook, passed down from assistant to assistant, outlining expectations for the role.

The day began early. Wintour typically woke between 4 and 5:30 a.m., read the news, played tennis, and arrived at the office around 8 a.m. By then, assistants had already prepared her coffee, breakfast, and schedule.

Image credits: Getty/Jacopo Raule

@voguemagazine The moment we’ve all been waiting for…today, three of #AnnaWintour’s former assistants—Sache Taylor, Sammi Tapper, and Marley Marius, or “Anna’s Angels,” as Chloe Malle calls them—join #TheRunThrough to discuss what #TheDevilWearsPrada got right (and wrong) about working at #Vogue♬ original sound – Vogue

“When she asks for someone, she wants that person very quickly,” Marius said.

Taylor described physically tracking down editors to get them into meetings on time, sometimes hovering at their desks to make sure they moved faster. “I would just hover until they were ready,” she said.

Wintour’s assistants had to follow strict rules behind the glamour

Image credits: Vogue

While The Devil Wears Prada painted a high-fashion fantasy, some parts were grounded in reality.

There were clear expectations around appearance. Assistants were told “no jeans and no sneakers,” and heels were initially encouraged. However, practicality often took over.

Marius admitted she lasted just two weeks in heels before switching to flats due to the job’s fast pace. “Things are happening at a certain pace, and it sometimes involves a bit of running,” she explained.

Image credits: 20th Century Studios

The workload did not end at the office. Wintour carried what assistants called a “homework bag”, an L.L.Bean tote filled with articles, drafts, and the magazine’s “book”, a preview of upcoming issues.

“She never wants anyone waiting on her for feedback,” Tapper said.

According to the assistants, Wintour reviewed everything overnight, often returning detailed notes by the next morning. Her edits, however, were known for being difficult to read.

Image credits: 20th Century Studios

“It takes a village” to decode her handwriting, Taylor joked, adding she would only ask for clarification “once a week.”

Despite the intensity, some assistants described adapting their routines to keep up, sticking to simple outfits and focusing more on efficiency than fashion.

As behind-the-scenes stories resurfaced, Wintour addressed her Devil Wears Prada image and poked fun at herself

Image credits: Vogue

Ahead of The Devil Wears Prada 2, Wintour posed for a special Voguecover alongside Streep.

Reflecting on the comparison between herself and Miranda Priestly, Wintour told Greta Gerwig, “It’s such an honor to be played by Meryl, however distant Miranda is from myself.”

She also admitted she was curious and slightly nervous about the upcoming sequel, even calling Streep directly to ask about it.

Image credits: Vogue

“She read the script… and said, ‘Anna, I think it’s going to be all right,’” Wintour shared.

At the same time, she dismissed any idea of stepping into acting herself. “I have no gifts… I can’t sing, I can’t dance, I can’t act,” she said.

Streep, in turn, joked about the reality of Wintour’s job, saying she “would dread the shoes,” highlighting the role’s demanding nature.

With interest around the film growing, fans picked up on an unexpected detail in the trailer of The Devil Wears Prada 2

Image credits: 20th Century Studios

In one scene showing Anne Hathaway’s character crossing a New York street, a bystander inside a taxi can be seen holding a phone out of the window, seemingly filming the moment.

“This girl having her phone just wide out the window in the trailer is frying me,” one viewer wrote.

Image credits: 20th Century Studios

Others quickly joined in. “And the camera captured her completely!” another added, while one joked, “Because that’s Andy Sachs. A million girls would kill for that job!”

The Devil Wears Prada 2 is set to release on May 1, nearly 20 years after the original became a cult classic.

“Why does this make me want to apply for the job?” wrote one user

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