Anna Wintour's Biggest Career Risks (That Totally Paid Off)

As the most powerful woman in fashion, Anna Wintour influences far more than the sphere of style, from finance to politics and more—making her one of today’s most powerful women, period. Editor in chief of Vogue, creative director of Condé Nast, a philanthropist, a political advocate, and even an appointed officer of the Order of the British Empire… We’re all familiar with Wintour’s position now, but some might not realise all the risks she’s taken to get here. This brings us today’s story—a roundup of her biggest career risks, all of which (no surprise) have paid off for her.

Scroll through to read about them!

1966: Drops out of school


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In 1966, Wintour dropped out of the prestigious North London Collegiate School to focus on fashion and begin a training program at Harrods. Four years later, she would begin her career in fashion journalism by landing a job as an editorial assistant at Harpers & Queen magazine.

1975: Quits job and moves to New York City

After a successful stint at Harpers & Queen, Anna, who had been disagreeing with her boss, decided to quit and move to New York City with her boyfriend at the time.

Late '70s: Works at an erotic magazine

Between jobs, Wintour had a brief stint working for women's adult magazine Viva. Despite the publication's reputation, while there, she was able to convince top photographers including Helmut Newton to shoot for its spreads.

1987: Makes drastic changes to House & Garden

As the head of House & Garden magazine, she shifted the focus of its editorials to be heavily about fashion, even renaming the publication HG. In the end, this negatively affected sales but simultaneously boosted her reputation as a fashion editor in the industry. From there, she went on to work for Vogue

1988: Puts a model in jeans on the cover of Vogue

For her first cover after replacing Grace Mirabella as editor in chief of American Vogue, Wintour chose an image featuring a model in jeans. This was the first time a model had worn anything so casual and inexpensive on the cover of the magazine—the printers had to double-check that it wasn't an error—and marked the beginning of the many changes to come under Wintour.

1989: Features Madonna on the cover of Vogue

By placing Madonna on the cover, Wintour broke decades of tradition: only models had ever landed the coveted spot before. This risk has become one of Wintour's biggest legacies, as she set the tone for an unprecedented relationship between celebrities and fashion.

2004: Publishes largest-ever monthly magazine issue

The September 2004 issue of Vogue was a record-breaking 832 pages—at the time the largest-ever issue of a monthly publication. Wintour's 2007 September issue has since become the subject of a documentary, in which she appeared in 2009.

2009: Creates Fashion's Night Out after recession


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As a response to the recession's immense impact on fashion industry sales, Wintour urged shoppers to actually spend when she developed Fashion's Night Out—a global initiative designed to bring consumers to stores to celebrate (and spend on) fashion through a series of events. 

Shop some fashion books we think Anna Wintour would approve of…

Which fact most surprised you? Tell us in the comments! 

Opening Image: Action Press/Rex/Shutterstock

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