From Mistake to Masterpiece

The story behind Anna Wintour’s first Vogue cover is a tale of bold decisions, risk-taking, and a stroke of serendipity that helped redefine the world of fashion magazines.

When Wintour became editor-in-chief of Vogue in 1988, she brought with her a vision that would shake up the magazine’s traditional approach, and her very first cover reflected that dramatic shift.

What happened? Read on and find out…

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THE BOLD MOVE

At the time, Vogue covers typically featured models styled in luxurious, glamorous clothing, often shot in elegant, controlled poses. The magazine was known for its high-fashion image and air of sophistication.

But Anna Wintour had different ideas. She wanted to make Vogue more relatable, fresh, and accessible to a broader audience, not just to the elite.

For her first cover, shot by photographer Peter Lindbergh, Wintour chose Israeli model Michaela Bercu, who was a relatively unknown face at the time. What was even more unconventional was the outfit Bercu wore: a bejeweled haute couture Christian Lacroix jacket paired with simple, faded denim jeans.

This was a far cry from the formal, ultra-glamorous looks Vogue was known for showcasing on its cover. The jacket was high-fashion, but the jeans were casual and unexpected—a juxtaposition that was unheard of at the time in a Vogue cover. The choice of jeans wasn’t entirely deliberate either; Bercu had shown up to the shoot unable to fit into the matching skirt due to weight gain after a vacation, and Wintour decided to roll with it.

THE SHOT THAT MADE HISTORY

In addition to the daring fashion choice, Bercu’s pose was equally unconventional. She was laughing and slightly blurred in the image—a spontaneous moment captured by Lindbergh during the shoot. The final result was a far cry from the posed, polished perfection that had dominated Vogue covers up until that point. Wintour didn’t see it as a mistake; she saw it as an opportunity to bring a sense of realness and spontaneity to fashion.

This gamble on a more relaxed and relatable aesthetic was a huge risk. The image broke the fashion rules of the time, mixing high and low fashion in a way that had rarely been seen on a major magazine cover, let alone one as prestigious as Vogue. Many people within the industry were shocked and some even questioned Wintour’s decision.

THE RESULT: A GAME-CHANGING MOMENT

But Anna Wintour’s instincts were right. That cover was a game-changer and set the tone for the future of Vogue under her leadership. The jeans, the natural styling, and the carefree vibe of the cover helped bridge the gap between high fashion and street style, making Vogue more accessible to everyday readers.

In her own words, Wintour later explained the significance of that cover:
"It was about a different way of looking at a girl, a different way of looking at fashion. And this reflected my own life. I’d just come back from a trip to Italy, and I was wearing jeans. It was about mixing high and low. Not necessarily dressing head-to-toe in designer clothes, but mixing what you wear in the way that most people do today."

Wintour’s decision to break away from the traditional norms wasn’t just a passing trend—it was the beginning of a new era for Vogue and for fashion magazines as a whole. The cover symbolized the evolution of fashion toward a more inclusive, versatile, and dynamic world. It also solidified Wintour’s reputation as a visionary, someone who could anticipate where culture and fashion were headed.

LEGACY

That first cover is now considered iconic and marks the beginning of Anna Wintour’s decades-long tenure as Vogue’s editor-in-chief. Her decision to take risks, blend high fashion with everyday style, and capture spontaneous, authentic moments would become defining characteristics of her editorial approach. Wintour’s Vogue would go on to become one of the most influential fashion publications in the world, continuing to push the boundaries of what fashion could be.

This seemingly small yet significant decision—to put a laughing model in jeans on the cover of Vogue—changed not only the trajectory of the magazine but also helped to democratize fashion, proving that even in a world as polished and highbrow as fashion, serendipity and spontaneity can lead to transformative success.

TOO LONG; DIDN’T READ (TL;DR)

Anna Wintour’s first Vogue cover in 1988 was a bold departure from tradition, featuring model Michaela Bercu wearing a Christian Lacroix jacket paired with casual jeans.

This mix of high fashion and everyday style was unconventional for the magazine, as was the spontaneous shot of Bercu laughing. Wintour’s decision to embrace this more relatable, authentic image symbolized her vision of making fashion accessible to a broader audience.

Though risky at the time, the cover became iconic and marked the beginning of a new era for Vogue, solidifying Wintour’s reputation as a visionary in the fashion industry.

Some fun facts about Vogue magazine:

• It’s Over 130 Years Old: Vogue was first published in 1892 as a weekly newspaper in the U.S., focused on high society and fashion. It later became a monthly magazine in 1916, and today it’s a global fashion powerhouse with editions in over 25 countries.

• The Famous Madonna Song: Madonna's 1990 hit song "Vogue" was inspired by the fashion magazine’s influence on pop culture. The song celebrated the glamorous lifestyle associated with Vogue and popularized "voguing," a dance style from the New York ballroom scene.

• The September Issue: Vogue’s September issue is famously known as the most important and largest edition of the year. In 2012, the U.S. edition's September issue broke records with 916 pages, weighing over 4 pounds!

• Red Carpet Trends: Many of the iconic red carpet trends you see during awards season are influenced by Vogue. The magazine's yearly Met Gala, often dubbed "fashion's biggest night," sets the tone for red carpet styles with its celebrity-studded guest list and cutting-edge fashion themes.

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