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, she had already made a name for herself as an editor who intuitively 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, as Wintour prepares to step back from editorial decisions, the future of Vogue enters uncertain waters. Chloe Malle, the newly appointed head of editorial content, faces the challenge of keeping the magazine relevant amidst fierce competition from digital platforms like TikTok and Instagram.

While the fashion world used to revolve around printed publications, today, the landscape is vastly different, with audiences expecting instant access to content. Print magazines, once revered, have become relics struggling to find their place.

Malle has hinted at changes including less frequent issues focused on significant cultural themes, hinting at a desire to shift Vogue's image to something more collectible than disposable.

Throughout her tenure, Wintour expanded Vogue's cover roster, showcasing a blend of royalty, politicians, pop stars, and more, often stirring debate over her choices. The notable features of Kanye West and Kim Kardashian in particular sparked discussions about the magazine's direction.

The question remains whether Vogue can still thrive without the indelible mark left by Wintour. As the industry looks forward to a new era under Malle, how she navigates these changes will dictate if Vogue continues to hold its iconic status or if it becomes another victim of the digital age.