Anna Wintour's 10 Most Influential Covers

Well, I was wrong.

I thought Anna Wintour would make a splash for her last Vogue cover and book, like, Kate Middleton or, I don’t know, Oprah. Taylor Swift’s wedding dress reveal? Someone or something… mega.

I did not expect a solo man, Timothée Chalamet, floating around in outer space like a paper cut-out superimposed onto a 1,000-piece puzzle or an old mousepad.

But that’s Anna. She probably didn’t want to make a big deal over her last-ever cover as editor-in-chief before the task passed to her new head of editorial content, Chloe Malle, because that’s not her style. She’s the type of person who would rather throw a birthday party for Baz Luhrmann instead of for herself. She doesn’t like looking back or reflecting — she always talks about moving forward. To wit, the confirmation we got that this was, in fact, her last cover was buried as an aside in an episode of the Vogue podcast.

The reaction to Anna’s last cover has been, well, mixed at best. I saw a lot of comments about how it’s “giving Canva.” People did not appreciate the austerity of the inside photo spread, which Anna favorite Annie Leibovitz photographed at a land art installation in Nevada by artist Michael Heizer. Still others wondered why she decided to put a white man solo on her final cover. (Vogue has only featured men by themselves on three covers ever: Harry Styles for December 2020; Colman Domingo, A$AP Rocky, Pharrell Williams, and Lewis Hamilton for May 20205, pegged to the Met’s Black dandy exhibition and gala; and now Timmy.)

Chalamet is promoting his awards-bait movie with Gwyneth Paltrow being released Christmas Day, Marty Supreme, in which he plays a ping-pong player. (Maybe he’s like a ping-pong ball in space, floating through the fashion ether, from Chanel face to Vogue cover and back again?)

Still, the cover is very Anna. It caps off a decades-long collaboration with Annie Leibovitz, mixes art and fashion (which she loves), and features an A-list star promoting a movie that seems tasteful.

Anna has succeeded many times with this formula. But it’s one that makes less and less sense in 2025, when so few movies — and almost none that aren’t targeted to kids — open at the box office. Awards season is more and more a celebration of films few have seen by an industry prostrated before Big Tech as it carves it up like roast beef. Anna’s Met Gala now even overshadows award season red carpets.

This Chalamet cover is historic, albeit not for its influence. That said, Anna’s tenure at Vogue, which she edited for 37 years, has been incredibly influential. Ahead, my list of her ten most impactful covers through her years as an editor-in-chief.

10 - HG, March 1988

When Anna took over House & Garden in 1987, she thought (correctly, I’d argue) the photos were stuffy and lifeless. Dining tables were set with no sign of human activity and not a dinner napkin out of place.

She decided to introduce people to interiors photography, including celebrities and socialites. When I was reporting Anna, one person told me it was radical for her to include a photo of a laundry room where the detergent was visible — the point is, these homes were lived in, they didn’t exist as totems to furniture.

Though the interior design community was aghast at her changes at the time, including shortening the title to HG, she established a new formula that home magazines like Elle Decor and Architectural Digest still use today. Those magazines are less about fantastic interiors than photographs of celebrities by their fireplaces, whether their homes are uniquely designed or just forgettable venues for high-contrast marble and kitchens with no food in them.

9 - Anna’s first British Vogue cover, August 1986

Anna ran British Vogue briefly beginning in 1986 — her first editor-in-chief role — after serving as American Vogue’s creative director under Grace Mirabella. She took a magazine that featured fashion that was often just silly and horse-y and made it over to appeal to the modern working woman. While this upset a change-averse contingent in British media, it also setting a new standard at the title and helped to globalize her particular, no-nonsense aesthetic.

8 - Anna’s first Vogue cover, November 1988

This cover was revolutionary for its time. Grace Mirabella had been publishing tightly-cropped headshots of models for each issue, photographed in a studio by Richard Avedon. Anna came in, canceled Avedon’s contract, and decided to photograph model Michaela Bercu outside in a Christian Lacroix top and Guess jeans — mixing high and low, showcasing a casual vision of glamour that would inform her Vogue moving forward.

7 - Madonna, May 1989

This was Anna’s first celebrity cover — and a radical move for the time. Madonna was highly controversial, having just released her “Like a Prayer” music video with religious imagery that got her Pepsi endorsement deal canceled. Rather than shy from the controversy, Anna rightly realized she could expand the public’s idea of who belongs in Vogue.

6 - Ivana Trump, May 1990, and Melania Trump, February 2005 (Tie)

Anna put Ivana Trump on the cover around the time of her split from Donald Trump — then just a media-hungry, New York real estate guy — even though she feared she was “too tacky,” she told one of her editors at the time, as I reported in Anna: The Biography. As committed as Anna is to a particular taste level, she’s been just as committed to occasionally breaking with it. Her instincts in this regard have often proven correct: The intrigue around Ivana was so great that the issue sold 750,000 copies, which was strong for the time.

Melania Trump’s 2005 cover, however, sold only 417,000 copies. But I’m putting it on the list because, like it or not, Anna contributed to the Trump family’s rise, the myth of Donald Trump as a guy who knows business well enough to get rich and land model wives dripping in couture and diamonds and Birkin bags. I wonder if, as a ardent Democrat, Anna regrets this cover today.

5 - Gwyneth Paltrow, August 1996

Anna photographed Gwyneth three times before she finally gave her a Vogue cover for August 1996, pegged to Emma. This cover reflected the formula that Anna relied on for the next two decades — a tastefully styled A-list movie star (musicians and TV actors were rarely given top billing in these years), promoting a tasteful movie.

4 - Naomi Campbell, September 1989

Naomi was the first Black model to appear on the cover of Vogue’s September issue, the magazine’s most important issue of the year. Black stars seldom covered Vogue with regularity until very recent history, making their rare appearances all the more notable in Anna’s earlier tenure. When she made the rare move of featuring a Black woman on the cover in the eighties and nineties, it only drove attention to their lack of representation in Vogue and fashion more broadly.

Around the time Ugandan model Kiara Kabukuru got the cover for July 1997, Amy Spindler wrote in the New York Times about how fashion appropriated African culture on the runway and in editorials. She added:

In response to that issue, Vogue even printed a letter from a reader who wrote, “From Naomi Campbell in an animal-skin bikini to that bizarre and unworldly layout with the Asian model a few months ago, to the distasteful, racist and colonialist depiction of a woman in Ralph Lauren’s idiotic and patronizing interpretation of Masai clothing, you consistently blow it when it comes to women of color.”

3 - The Supers, April 1992

In honor of its 100th anniversary, Vogue gathered ten supermodels to pose in white jeans and tied-up shirts, a recreation of an iconic Irving Penn photo. It was sort of the last gasp of this era of fashion in which models reigned — before celebrities took over covers, ad campaigns, front rows, and Vogue generally. When I was researching Anna, I learned that Anna actually wasn’t thrilled initially about the switch from models to celebrities, despite how she helped shepherd in that era. She generally preferred the results her team got with models, for whom posing and making clothes look great came second nature.

2 - Kim Kardashian and Kanye West, April 2014

Anna has talked about how controversial she knew this cover would be — how she knew people would be “horrified.” But she also admitted that Kim’s wedding to Kanye was such an important cultural moment that she felt she couldn’t ignore it.

Whether it benefited her or Kardashian more, I’m not sure. Some Vogue readers to this day say the magazine hasn’t been the same since, citing this cover as the moment it all went to hell. Meanwhile, Kardashian is probably one of the most famous and influential fashion “icons” wearing clothes today, sitting atop Skims, a more than $3 billion clothing business. Anna’s approval undoubtedly helped her get taken seriously by the fashion industry and consumers, and this cover was a clear turning point in her relationship to the industry.

1 - Michelle Obama: March 2009, April 2013, December 2016

Michelle Obama appeared on the cover of Vogue three times as first lady (Anna raised money for both of Barack Obama’s presidential campaigns). These issues are now collectibles and helped cement Obama’s status as the biggest political fashion influencer since Jackie Kennedy. She is to this day one of the world’s most important fashion influencers — period. These covers were also a flex for Anna, showing her ability to feature one of the most important and sought-after fashion icons of her generation in three separate photo shoots. They were also a great showcase for American fashion, both Michelle and Anna being terrific champions of American design.

With American fashion even less dominant now than it was then (it has always struggled to compete with European houses), these issues succeeded because they captured so well specific moments in time, culture, and history.

Which covers would you add to the list? Would love your thoughts in the comments!

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