A look at the editor-in-chief’s Vogue covers from her first radical combination in 1988 to her final ‘weird’ shoot

During her 37-year tenure as editor-in-chief of American Vogue, Anna Wintour has presided 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 Wintour’s 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.

Closeup of studded stilettos in trailer for The Devil Wears Prada 2 causes fashion debate on social media

Posting the first trailer for The Devil Wears Prada 2 on Instagram on her birthday this week, the film’s star Anne Hathaway captioned the video with “it’s everybody’s birthday”, prompting copious comments featuring emojis of flames, hearts and – of course – the red shoe now associated with the film’s poster.

But with the trailer circulating on social media, it’s the shoes that have become the focus of fashion debate – and not in a good way.