Anna Wintour’s First U.S Vogue Cover in November 1988, Featuring Model Michaela Bercu

Anna Wintour’s first-ever cover for Vogue (Nov. 1988) marked the first time—gasp!—jeans appeared on a Vogue cover and the first time anyone mixed high-low in such a brazen manner: $50 jeans with a $10,000 jacket.

She used less well-known models, and mixed inexpensive clothes with high fashion: the first issue she was in charge of, November 1988, featured a Peter Lindbergh photograph of 19-year-old Michaela Bercu in a $50 pair of faded jeans and a bejeweled T-shirt by Christian Lacroix worth $10,000. It was the first time a Vogue cover model had worn jeans; when the printer saw it they called the magazine’s offices, thinking it was the wrong image.

In 2012, Wintour reflected on the cover:

“It was so unlike the studied and elegant close-ups that were typical of Vogue’s covers back then, with tons of makeup and major jewelry. This one broke all the rules. Michaela wasn’t looking at you, and worse, she had her eyes almost closed. Her hair was blowing across her face. It looked easy, casual, a moment that had been snapped on the street, which it had been, and which was the whole point. Afterwards, in the way that these things can happen, people applied all sorts of interpretations: It was about mixing high and low, Michaela was pregnant, it was a religious statement. But none of these things was true. I had just looked at that picture and sensed the winds of change. And you can't ask for more from a cover image than that.”

Years later, Wintour admitted the photo had never been planned as the cover shot. In 2011, when Vogue put its entire archive online, Wintour was quoted as saying, “I just said, ‘Well, let’s just try this.’ And off we went. It was just very natural. To me it just said, ‘This is something new. This is something different.’ The printers called to make sure that was supposed to be the cover, as they thought a mistake might have been made.”

In 2015, she said if she had to pick a favorite of her covers, it would be that one. “[I]t was a leap of faith and it was certainly a big change for Vogue.”ˆ

Wintour took over as Editor-in-Chief of Vogue in 1988. Her shift toward a more youthful, accessible vibe sparked controversy in the fashion world, which had been used to Vogue’s traditionally high-brow, exclusive image.