From Kim Kardashian to Melania Trump, we look back at Anna Wintour’s most iconic, memorable and controversial cover moments throughout her 37-year tenure.
November 1988
Wintour’s first cover for Vogue, in November 1988, was a departure from the hyper-produced, editorialised images that were typical of the magazine’s covers at the time. Shot by Peter Lindbergh and styled by Carlyne Cerf de Dudzeele, model Michaela Bercu wears a haute couture Christian Lacroix jacket with a beaded cross and stonewashed Guess jeans. While it may be common today, the styling of high fashion with off-the-rack denim was rare at the time.
As Wintour recounted to Vogue in 2012, so revolutionary was the image that the magazine’s printers even called up to check if there had been a mistake. “I had just looked at that picture and sensed the winds of change,” she said.
May 1989
Throughout her tenure at Vogue, Wintour became known for putting celebrities front and centre on the cover – a risky move at a time when high fashion editorials featuring models was the norm. The May 1989 cover of the magazine, featuring a young Madonna at home, was an early sign of Wintour’s propensity to be at the forefront of change.
September 1989
In September 1989, Wintour put a young Naomi Campbell on the cover, dressed in an orange sequin Anne Klein suit and shot by Patrick Demarchelier. It was a first for both parties – Wintour’s first September issue and Campbell’s first American Vogue cover.
In 2020, Wintour appeared on an episode of the supermodel’s TV show, No Filter with Naomi, and revealed her decision to put a black model on the magazine’s cover was called into question by some board members (Beverly Johnson was the first black model to appear on the cover of US Vogue in 1974).
“I just thought, ‘this is a fantastic girl, this is the model of the moment, this is a great image’. And we made history together, so thank you,” said Wintour.
November 2001
In 2001, a then 19-year-old Britney Spears was at the height of her fame. So it was only fitting she graced the cover of the November issue. Shot by Herb Ritts, rosy-cheeked and smiling against the star-spangled banner, the cover came months after Spears’ infamous performance at the MTV Video Music Awards, in which she appeared scantily clad on stage with a real snake. This was a different side to Britney: the all-American girl next door.
“I don’t want to be considered a role model,” the pop star told Vogue. “I do this because it’s fun, and when I go on stage, I’m expressing myself and I can’t please everyone.”
February 2005
Back in 2005, Melania Trump appeared on the cover of Vogue in a lavish custom-made Christian Dior wedding gown. “Melania Knauss, the next Mrs. Trump, is a smashing 34-year-old Slovenian who handles her position (and the Donald) with panache,” wrote Sally Singer in the accompanying story.
Notably, the former model has not appeared on the cover of US Vogue since, despite Wintour and the Trumps previously being friendly. Jill Biden and Michelle Obama both appeared on the magazine’s cover three times each during their tenures as first ladies.
April 2008
Wintour’s April 2008 cover of Vogue, featuring basketball player LeBron James and supermodel Gisèle Bündchen, is considered one of her most controversial for its resemblance to an old King Kong poster and 1917 World War I recruitment poster that perpetuated the racist stereotype of a black man running off with a white woman.
Vogue spokesman Patrick O’Connell said at the time the magazine “sought to celebrate two superstars at the top of their game” for the magazine’s annual issue devoted to size and shape.
“We think Lebron James and Gisele Bundchen look beautiful together and we are honored to have them on the cover,” he said.
James said told an Ohio newspaper at the time that he was pleased with the cover, saying he was “just showing a little emotion”.
“Everything my name is on is going to be criticised in a good way or bad way,” James said. “Who cares what anyone says?”
March 2009
The March 2009 issue starring Michelle Obama was only the second time a first lady had appeared on the cover of the magazine, after Hillary Clinton in 1998. Obama would go on to feature on the cover twice more. Here, she appears in a magenta Jason Wu dress, the same designer behind her inaugural ball gown.
April 2014
Kim Kardashian and Kanye West’s appearance on the April 2014 cover of Vogue, shot by Annie Leibovitz, was a watershed moment for the magazine. For years, the publication had sought to distance itself from the ostensibly low-brow world of reality television that had given birth to the Kardashian empire.
“Kim and Kanye were a part of the conversation of the day. And for Vogue not to recognise that would have been a big misstep. You are leading, not following – and that’s a very important lesson to always keep in your mind,” Wintour has since said.
Published a month before the now-divorced couple’s nuptials, Kardashian appears in a white Lanvin dress, her lavish engagement ring front and centre, with West’s arms wrapped around her.
March 2018
The March 2018 issue, starring actor Alicia Vikander, may seem fairly innocuous at first, but the cover was criticised for its use of Photoshop, with Vikander’s arm appearing rather long. Throughout her tenure at Vogue, Wintour faced backlash for what were sometimes perceived to be overly airbrushed photo shoots, particularly of older figures like Hillary Clinton. Wintour has defended her use of Photoshop, stating it is only ever used to airbrush small “imperfections” but not to make women appear thinner.
September 2018
In September 2018, Beyoncé appeared on the cover of Vogue, shot by Tyler Mitchell, the first-ever African American photographer to produce a cover for the magazine.
“It’s important to me that I help open doors for younger artists. There are so many cultural and societal barriers to entry that I like to do what I can to level the playing field, to present a different point of view for people who may feel like their voices don’t matter,” said Beyoncé of her decision to work with the then 23-year-old Mitchell.
December 2020
Gracing the December 2020 issue of Vogue in a black tuxedo jacket and Gucci lace dress, pop star Harry Styles’ appearance was notable for two reasons: he was the first man to grace the magazine’s cover solo, and he was both criticised and lauded for his championing of gender-fluid fashion.
Despite the controversy, the cover certainly cemented Styles as a fashion icon, who was voted GQ’s “Most Stylish Man of the Year 2020” and included in The Business of Fashion’s “Class of 2022″ index.
His blue Gucci dress appeared in the Fashioning Masculinities: The Art of Menswear exhibition at London’s Victoria & Albert Museum.
October 2024
In October 2024, then vice president and democratic presidential nominee Kamala Harris appeared on the cover of Vogue for the second time.
Shot by Annie Lebovitz, Harris wore her own chocolate brown suit under the cover line “the candidate for our times” – a clear political endorsement from the publication.
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