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, contemporary, and accessible.
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. Her heir, Chloe Malle, is set to take over as head of editorial content.
Some see Wintour's continued presence as a reluctance to relinquish complete control; others see it as a necessity to avoid losing the magazine's remaining clout.
Once, fashion magazines like Vogue dictated trends without contest. However, opinions vary on whether it remains an arbiter of style today. Critics argue that with the rise of social media, print magazines face challenges in staying relevant in a rapidly changing world. Malle's tenure will see her reorienting Vogue into a format that embraces thematic issues rather than adhering strictly to monthly editions.
Wintour's legacy includes expanding the variety of cover stars, bridging fashion and entertainment, and sometimes sparking controversy, as seen with her decision to feature Kanye West and Kim Kardashian.
The direction Vogue takes under Malle will depend on its ability to utilize the magazine's prestigious history while navigating the evolving landscape of fashion and culture.
As discussions continue about potential cover features and the magazine's push for inclusivity, the real test will be whether Vogue can maintain its essence and influence moving forward, especially in a corporate world increasingly criticized for celebrating wealth over style.
I think we're about to see how much of the relevance of Vogue comes from Dame Anna, says Odell, summarizing the pivotal moment Vogue finds itself at.