How Anna Wintour’s First Vogue Cover Revolutionized Fashion

By Christopher Turner

Vogue is more than a simple fashion statement; the magazine is a culture influencer. There are countless examples of Vogue’s influence throughout its 130-year history, but one of the most significant is Anna Wintour’s very first cover. With the November 1988 issue, Wintour initiated a cultural milestone by putting a pair of stone-washed jeans on the cover of the legendary fashion magazine. Shocking at the time, the issue would go on to be one of the most famous fashion magazine covers of all time.

But, first the backstory.

Wintour took over the helm of American Vogue – somewhat brutally – with a surprise announcement at the end of June 1988, replacing Grace Mirabella, the famed fashion editor who had been the magazine’s editor-in-chief since 1971. Mirabella had revolutionized the magazine but by the mid-’80s, her approach was deemed “beige” and boring by the executives at Condé Nast (Vogue’s owner), and Wintour was quite suddenly brought in to revitalize the magazine with a more youthful, approachable edge that would, it was hoped, appeal to readers and advertisers.

Wintour’s first official issue as editor-in-chief was the November 1988 issue (which hit newsstands a month prior), and it garnered a ton of attention. The cover featured Israeli model Michaela Bercu wearing a $10,000 couture black silk Christian Lacroix jacket, bejewelled with a colourful cross and a pair of $50 stonewashed Guess jeans. It was the first time jeans had ever appeared on the cover of Vogue.

The shoot, which was lensed by photographer Peter Lindbergh and styled by flashy fashion editor Carlyne Cerf de Dudzeele, was originally intended to be for an inside story, and the Christian Lacroix jacket was originally supposed to be paired with a matching skirt. However, Wintour scrapped the skirt on the day of the shoot for being “disgusting.”

“The jacket was actually part of a suit, but the skirt didn’t fit Michaela; she had been on vacation back home in Israel and had gained a little weight,” Wintour recalled when she took a trip down memory lane for Vogue’s 120th anniversary in 2012.

So, the jeans were a last-minute swap when Bercu couldn’t fit into the matching skirt.

“The powers that be were a little surprised – the printers even questioned this picture – but it made a statement. It made a statement that it was a different time: we had a different view on fashion that we wanted to be much more accessible, much more free,” Wintour explained.

The move was unprecedented, and when the image hit newsstands, it was a shock to the fashion community. Jeans had never graced the cover of the legendary fashion bible; at the time, jeans were simply deemed “too casual” and contrary to the magazine’s fantasy as offered within its glossy pages. Wintour’s decision to put the image on the cover shifted Vogue’s attitude by showcasing fashion’s accessibility on the street. Whether she initially intended to or not, Wintour rebranded the magazine’s attitude for evolving readers.

Of course, the issue was a hit.

“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,” said Wintour.

As for the execs upstairs…they approved. According to Amy Odell’s 2022 book Anna: The Biography, S. I. Newhouse, the late owner of Condé Nast and the man who essentially made Wintour by taking a calculated risk on her, sent her a note after the issue had hit the newsstands. Wintour proudly displayed Newhouse’s note on her desk for years: “You knocked it out of the park, Anna. I’m so proud.”

Tags: Anna Wintour, top story, topstory, Vogue

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