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."
