In May 1989, Dame Anna Wintour did something that would become a hallmark of her time as editor-in-chief of US Vogue - she put a pop star on the cover.

Just a year into her tenure as the top of the magazine's masthead, Dame Anna had already made a name for herself as an editor who instinctively understood the zeitgeist. She was the first to put a model in jeans on Vogue's front, and now, Madonna.

If it was edgy to do jeans for November 1988, I think it was even edgier for her to do Madonna, says Amy Odell, author of Anna: The Biography.

For Marian Kwei, a stylist and Vogue contributor, this move speaks to Dame Anna's ability to make Vogue relevant to our times, make it contemporary, make it accessible. Before, it was women who could buy couture who were interested in what Vogue had to say, she says. But Dame Anna realised the need to reach out to the kids listening to Madonna.

Now almost 40 years later, Dame Anna is preparing to hang up her Manolo Blahnik's, sort of – while she will no longer be editor-in-chief, she will remain on as global editorial director. Down the hall will sit her heir, the 39-year-old Chloe Malle, who is stepping in as head of editorial content.

While some have attributed her continued presence as a sign of unwillingness to cede total control, one could also see it as a recognition of her unmatched place in the fashion industry, and the fear that should she go entirely, this print magazine – already a relic to some – will lose its remaining clout.

Vogue has historically been seen as the dominant force in fashion magazines, dictating trends to its audience rather than competing for attention. However, as digital platforms take precedence, the relevance of print media is increasingly questioned. Anja Aronowsky Cronberg, founder of academic publication Vestoj, states that no single magazine can hold the same relevance today as Vogue did in the past.

"There's no one magazine that is relevant in the way Vogue might have been relevant in the 80s," she comments.

Malle, now tasked with leading Vogue, reportedly aims to produce issues less frequently but with more thematic depth, elevating the magazine to a collectible status.

Wintour’s legacy includes a shift in Vogue’s cover choices, featuring an array of personalities from different backgrounds, indicating a blend of fashion and entertainment. Her controversial choices over the years have sparked discussions about diversity and commercialism.

The impending transition raises critical questions: How much of Vogue’s relevance is tied to Wintour, and can Malle navigate the changing tides of the fashion world while maintaining the magazine’s storied legacy?