Anna Wintour leaving Vogue as editor-in-chief: Her most memorable career moments
Anna Wintour doesn't break news, she makes it.
After nearly four decades at the helm of Vogue magazine, the editor-in-chief revealed her biggest news yet on Thursday, June 26: She will step down from her top editor role at the outlet by the year's end.
Known for her stern management style and iconic A-frame bob, she has revolutionized fashion and modernized Vogue with a keen eye for emerging designers and a disdain for existing trends.
Her name has become synonymous with the luxury fashion outlet – more visible than any other fashion editor in history – by producing risky covers and controversial spreads featuring Beyoncé, LeBron James, Simone Biles, former first lady Michelle Obama and A-list ex-couple Ye and Kim Kardashian.
Wintour will stay on as chief content officer at Condé Nast, the magazine's parent company, and as Vogue's global editorial director. WWD and Business of Fashion also confirmed the news.
As the style icon, 75, steps down this year, here is a look at the iconic moments that cemented her in fashion history.
How long has Anna Wintour been at Vogue?
Since her start at Vogue in 1988, Wintour has become synonymous with the high fashion scene, sitting stoically in the front row of New York Fashion Week shows, helming the Met Gala and presiding over the glossy pages of a magazine largely considered the "fashion bible."
Young Anna Wintour's 1988 first cover of American Vogue
Wintour's first cover as editor-in-chief is arguably one of her most edgy and experimental. For the cover shoot, Israeli model Michaela Bercu paired stonewashed Guess jean and a haute couture Christian Lacroix jacket adorned with a beaded cross. Wintour later said the look was "all very 'Like a Prayer'" in the vein of pop star Madonna's 1980s and early '90s religions-inspired era.
People had mixed reactions to the shoot, Wintour later wrote in a 2012 essay: "Afterwards, in the way that these things can happen, people applied all sorts of interpretations: It was about mixing high and low, Michaela was pregnant, it was a religious statement. But none of these things was true."
But Wintour had a simpler explanation: "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."
1995: Anna Wintour chairs her first Met Gala
The Met Gala started in 1948 as a fundraiser for the Metropolitan Museum of Art's Costume Institute, but under Wintour's more than three decades of leadership, it transformed into one of the world's most prestigious fashion events.
Wintour began co-chairing the fundraiser in 1995, wearing a floor-length, halter neck ivory gown that year to the "Haute Couture" themed event. She later went on to change the date of the gala from December to the first Monday in May each year, and, according to Vogue, tailored the guest list to include only the biggest stars in fashion, entertainment, sports and politics.
2003: Anna Wintour reportedly inspires 'Devil Wears Prada'
When Lauren Weisberger's bestselling book, "The Devil Wears Prada" hit shelves in 2003, and then movie screens in 2006, it introduced Wintour to an entirely new audience and turned her into an icon.
The story is based on Weisberger's experience as an assistant to Wintour at Vogue. Fans have long compared Wintor to Miranda Priestly, the icy, no-boundaries boss, played by Meryl Streep in the movie adaptation.
But the magazine giant didn't speak about those rumors until more than two decades later, when, at a musical adaption of the book in London, Wintour told the BBC it was "for the audience and for the people I work with to decide if there are any similarities between me and Miranda Priestly."
2014: Anna Wintour gives Kim Kardashian gift of a lifetime with Vogue cover
In present day, Kim Kardashian is a fashion icon in her own right. But in 2014, just over a decade ago, Wintour garnered backlash by granting the then-"Keeping Up with the Kardashians" star a Vogue cover with Ye, formerly known as Kanye West.
Ye and Kardashian appeared in a bridal embrace on the April cover that year, with Kardashian's 15-carat diamond engagement ring in full view. Inside were family photos of the pair and their eldest daughter, North West, taken by famed photographer and Wintour favorite Annie Leibovitz. Under the embrace were the hashtagged words: #WORLDSMOSTTALKEDABOUTCOUPLE.
Wintour's choice garnered backlash and simultaneously cemented Kardashian as a burgeoning star in the fashion world. Later, far more luxury brands began to work with Kardashian and her now-annual appearances at the A-list heavy Met Gala are among the most anticipated each year.
2017: Anna Wintour becomes a dame
The editor-in-chief and fashion icon was given a new title in 2017 by Queen Elizabeth II – a Dame Commander of the British Empire, the female equivalent of a knighthood.
Wintour received the honor at Buckingham Palace, wearing a pink belted Chanel coat and her classic sunglasses, for her service to journalism and fashion. Wintour was born in London and briefly led British Vogue.
2025: Anna Wintour Medal of Freedom honor
In January, Wintour joined designer Ralph Lauren, chef José Andrés, Irish singer and U2 frontman Bono, "Back to the Future" star Michael J. Fox, Oscar-winning actor Denzel Washington and TV personality Bill Nye to receive the Presidential Medal of Freedom from then-President Joe Biden.
Contributing: Anna Kaufman