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During her 37-year tenure as editor-in-chief of American Vogue, Anna Wintour has resided over more than 400 covers. December 2025’s, on newsstands this week, will prove her last before she steps away to focus on roles as Vogue’s global editorial director and chief content officer at Condé Nast.
The cover is certainly memorable: an image of the actor Timothée Chalamet photographed by long-term collaborator Annie Leibovitz in a Celine white polo neck, long cream coat and embroidered jeans, standing on a “planet” with a backdrop of a star-filled nebula provided by NASA.
It’s had something of a negative reception online. On Vogue’s Instagram, comments under the post include “I’m just horrified. It’s offensive with the budgets you have”, and “when you ask Chat GPT to do your cover”.
“It’s weird,” confirms Jeremy Leslie, the founder of magazine store, magCulture. “It’s so weird that after your initial ick, you start thinking, ‘well, but maybe she knows something that I don’t know’, but God help me, I don’t know what that is.”
There is an argument that the Chalamet image sits in the lineage of Wintour’s Vogue covers – with Leibovitz behind the lens and artistic references.
Part of the shoot features the actor in front of City, a land artwork by Michael Heizer in the Nevada desert, and the cover – to those familiar – wittily posits Chalamet, the prince of Hollywood, as The Little Prince, paying homage to Antoine de Saint-Exupéry’s classic illustration of a boy on the moon, for the cover of the 1943 book.
It has certainly got people talking – and that has been a consistent thread across Wintour’s covers. Her first for US Vogue paired Guess jeans with a Christian Lacroix sweater, a mix of high-low that was radical – and controversial – for a mainstream luxury fashion magazine in 1988. This was followed by images that defined their era: a post-scandal Madonna a year later, supermodels in 1992, a teenage Britney Spears with an American flag in 2001, Michelle Obama as a new first lady in 2009, Kanye West and Kim Kardashian on the eve of their wedding in 2014 and Beyoncé in a flower crown in 2018.
There were also moments that were criticised. The 2008 cover with LeBron James and Gisele Bündchen was seen as placing James in a racist King Kong trope with Bundchen as the defenceless white woman. The 2010 feature and shoot with Asma al-Assad, the wife of the Syrian dictator Bashar al-Assad was regarded as a misjudged puff piece. The Beyoncé cover, although lauded, was also notable because it was the first in the magazine’s history to be taken by a Black photographer, 23-year-old Tyler Mitchell. Meanwhile, the recent Lauren Sanchez Bezos cover was seen as a tone-deaf celebration of the mega rich.e
“Overall, Anna has played it very safe,” says Amy Odell, the author of Anna: The Biography and writer behind the Back Row substack. “But she’s poked the bear strategically and smartly. She has said you can’t do a controversial crazy cover every single month, but every so often you need to do it to keep people on their toes.”
With Chloe Malle now responsible for covers as the head of editorial content at Vogue – there is no longer an editor-in-chief position – it is her task to explore what becomes a talking point in 2026. Leslie believes Chalamet is a hard act to follow.
“I can’t help feeling that this cover is a huge statement,” he says. “Anna chucking her gloves on the floor and saying, ‘Go on then’, because it is an extraordinary cover, and it’s unlike any other Vogue cover.”
Odell says Malle will have the challenge of who fits Vogue’s idea of wealth and aspiration now. “[It used to be] you could photograph the heirs to a frozen food fortune on their yacht somewhere and be like, ‘they have such amazing style’. Now it’s nepo babies, it’s Lauren Sanchez, and people don’t find it tasteful any more … when they’re viewed as the American oligarchy, it offends people in a way that I don’t think it did for most of [Wintour’s] tenure.”
The new era could, however, mean less Wintour-style talking point covers full stop. “Times have changed,” says Leslie. “Condé Nast used to relish having these star editors … they’re more worker bees [now]. So in that respect, perhaps Chloe’s not going to look to make a statement.”
Wintour’s own focus might now turn to Vogue World. The series of Vogue-branded fashion shows, which begun in 2022, have different themes across different cities. The latest – Vogue Hollywood – featured stars such as Kendall Jenner and Nicole Kidman in an event raising money for the victims of the LA wildfires. Next up is Milan, with Vogue World focusing on craftsmanship taking place in the Italian city in September 2026.
