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, 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.
Now almost 40 years later, Dame Anna is preparing to hang up her Manolo Blahnik's - 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, stepping in as head of editorial content.
While some see her continued presence as a sign of unwillingness to relinquish control, others view it as recognition of her unmatched place in fashion, fearing that without her, this print magazine - already viewed as a relic by some - will lose its clout.
Once, fashion magazines like Vogue ruled the industry without needing to compete for attention. Today, some question its relevance, pointing to the rise of digital platforms like TikTok and Instagram.
In light of this changing landscape, Malle reportedly plans to publish issues less frequently, focusing on themes or events, aiming to make Vogue a collectible item rather than just another monthly release.
The transition to new leadership also raises questions about whether Vogue can continue to bridge the gap between fashion and the broader cultural conversation, a role Wintour has played effectively through diverse covers that span various socio-cultural figures.
Despite criticisms of Wintour's late response to diversity issues, her reign has undeniably left a mark on both fashion and pop culture. As Malle settles into her new role, the question remains: how much of Vogue's relevance is tied to Wintour's iconic presence? The legacy of the magazine hangs in the balance as it ventures into a new era.