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, alongside none other than 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.

This ability to make Vogue relevant to our times, make it contemporary, make it accessible has been recognized by industry insiders. Marian Kwei, a stylist and Vogue contributor, highlights how Wintour expanded the magazine's reach from exclusively affluent couture buyers to include the youth culture represented by Madonna's audience.

Now, almost 40 years later, Wintour is preparing to hand over the editing reins to Chloe Malle while retaining her title as global editorial director. This transition has sparked debate about whether Wintour's semi-retirement signifies a reluctance to let go of control, or if it's an acknowledgment of her influential status in the fashion industry.

Wintour's presence at the helm has been crucial for Vogue, especially as print magazines face increasing financial pressures and competition from digital media platforms. Critics debate Vogue's relevance, but supporters like Odell affirm its importance in today's fashion landscape.

In light of these challenges, Malle plans to pivot the magazine's approach, potentially releasing issues less frequently but concentrating on themes and significant cultural moments, fostering a sense of collectability around the print medium.

As Malle moves forward, she inherits a legacy intertwined with Wintour's iconic influence. The future trajectory of Vogue will depend heavily on Malle's ability to navigate and leverage this legacy while engaging with the rapidly changing landscape of fashion media.