After 37 years as Vogue’s editor in chief, Anna Wintour is officially stepping down. The fashion icon is not retiring altogether; instead, she will remain on as the publisher’s global chief content officer as well as Vogue’s global editorial director, per CNN.
It is, nonetheless, the end of an era — one marked by Met Galas, groundbreaking (and sometimes controversial) magazine covers, and moments that cemented the EIC’s place in pop culture history. From being dubbed “Nuclear Wintour” by tabloids in the ’90s for her icy management style to inspiring one of Meryl Streep’s most famous roles, Wintour’s reign at Vogue has shaped not only fashion but how the world views it.
Anna Wintour becomes a tabloid fascination
Prior to her reign as editor in chief of Vogue, Wintour worked across different magazines at Condé Nast, including House & Garden and the U.K. edition of Vogue. It was during her time at the U.K. fashion magazine, where she replaced beloved editor Bea Miller, that British tabloids gave her the titles “Nuclear Wintour” and “Wintour of Our Discontent” — nods to her reputation for being cold, demanding and unapologetically tough on her staff.
In 1997, the British-born Wintour pushed back against the nicknames in a piece for the Guardian, writing that while journalists portrayed her as a “wicked woman of steel,” she only recalled letting go of “two or three” employees during her time at the magazine.
Wintour at the 19th Annual CFDA Fashion Awards at Lincoln Center in New York City. (KMazur/WireImage)
“There was a cozy but mildly eccentric atmosphere at British Vogue, which, after my time in New York, struck me as out of date,” Wintour recalled. “It also seemed out of step with the fast developing social and political changes that were thundering through Britain in the eighties, under Margaret Thatcher. I felt the cozy approach was not responsive to intelligent women’s changing lives. So I decided to infuse the magazine with a bit of American worldliness, even toughness.”
While Wintour may not have appreciated the nicknames nor agreed with their accuracy, it’s clear that her tough-as-nails reputation solidified a certain image of the ice queen fashion editor — an image that Wintour would carry with her throughout her career.
Wintour goes rogue at Vogue
In 1988, Wintour debuted her first cover of Vogue — and it shocked the fashion world. Model Michaela Bercu wore a $10,000 Christian Lacroix couture jacket with a bejeweled cross along with $50 Guess jeans, photographed outside in natural light. The casual tone of the photo was a stark change for the magazine; even Wintour herself didn’t initially expect to run the photo on the cover.
“It was so unlike the studied and elegant close-ups that were typical of Vogue’s covers back then, with tons of makeup and major jewelry,” Wintour wrote of the cover in a 2012 Vogue piece, adding that the photo “broke all the rules.”
Wintour’s first Vogue cover stirred controversy and questions but ultimately became iconic. (Peter Lindbergh/Vogue)
The model “wasn’t looking at you, and worse, she had her eyes almost closed,” Wintour explained. “Her hair was blowing across her face. It looked easy, casual, a moment that had been snapped on the street, which it had been, and which was the whole point.”
Wintour said that the cover led to all sorts of incorrect interpretations, including that it was some sort of “religious statement.” None were true. Instead, she wrote, “I had just looked at that picture and sensed the winds of change. And you can’t ask for more from a cover image than that.”
‘The Devil Wears Prada’ hits theaters
In 2006, The Devil Wears Prada, a novel written by former Wintour assistant Lauren Weisberger, was adapted into a movie starring Anne Hathaway and Meryl Streep. Immediately, people assumed that Streep’s character Miranda Priestly — EIC of the fictional Runway magazine — was a thinly veiled caricature of Wintour.
Wintour has not said much publicly about the portrayal of Priestly, an icy, calculating and wildly demanding boss. In fact, Anna: The Biography author Amy Odell wrote that when the EIC learned that Weisberger had sold The Devil Wears Prada, “she said to [managing editor Laurie] Jones, ‘I cannot remember who that girl is,’” per Entertainment Weekly.
Recently, the film — for which a sequel is in the works — received a West End musical adaptation, which Wintour attended in December 2024. Speaking to the BBC after the show, she said it is “for the audience and for the people I work with to decide if there are any similarities between me and Miranda Priestly.”
The Devil Wears Prada is not the only piece of pop culture to apparently pay tribute to the famed fashionista. She was also parodied on the show Ugly Betty with the character “Fey Sommers.” Interpretations of Wintour, always with her signature giant sunglasses, have also been seen on Saturday Night Live and The Simpsons.
Wintour also appeared as herself in 2018’s Ocean’s 8, which was about a group of women pulling off a heist at the Met Gala.
‘The September Issue’ brings Wintour’s work to life
In 2009, R.J. Cutler’s documentary The September Issue followed Wintour as she and her team crafted the September 2007 edition of Vogue — at the time, the largest issue to date. It peeled back the curtain on working for Wintour, revealing her exacting standards and intense leadership style at the center of the high-pressure world of fashion publishing.
In a review of the documentary by Roger Ebert, the late film critic wrote, “There cannot have been a page she wasn’t involved with. This seems to be a woman who is concerned with one thing above all: The implementation of her opinion.”
Wintour makes her mark on the Met Gala
Fashion’s night out wouldn’t be quite the same without the influence of Wintour. In 1995, she took over as chair of the Met Gala, transforming the annual fundraiser for the Metropolitan Museum of Art’s Costume Institute from a modest society dinner into a global pop culture phenomenon.
Wintour revamped the guest list, inviting A-list celebrities, designers, models and entertainment industry power players. This coincided with the rise of the celebrity stylist, putting these behind-the-scenes fashion players on display just as much as the stars wearing their outfits. Wintour helped elevate pop culture icons like Rihanna, whose outfit choices have become among the most anticipated on the red carpet.
Wintour attends the 2025 Met Gala. (John Shearer/WireImage)
In 2015, Wintour made headlines with the Met Gala once again. “China: Through the Looking Glass” was one of the most attended exhibitions — but also a highly controversial one, as Wintour and her team were accused of promoting appropriation and showing Eastern culture through a Western lens.
Still, the Met Gala has continued to push cultural conversation forward, as it did this year with its theme “Superfine: Tailoring Black Style,” which spotlighted Black designers and Black identity. In May, Wintour told E! News of the exhibit, “It’s about optimism and hope and community. I hope that many, many people come and see it.”
