Anna Wintour – Huge Sunnies, Pageboy Haircut and High Heels.

Anna Wintour – the fashion icon that we know as the one in the front row at fashion week with the oversized sunglasses.

Although, to be honest, seems these days everyone is wearing sunglasses in the front row.

Anna Wintour in R. J. Cutler's THE SEPTEMBER ISSUE

Wintour was born in London on the 3rd of November 1949. Her father, editor of the London Evening Standard Newspaper, played a large role in deciding that she would one day work in fashion. During her teen years, Wintour made the decision to drop out of finishing school and decided that she was going to spend the 60’s in London. Her signature pageboy bob has been her hairstyle since the age of 15. When Wintour went out clubbing – she was partying with some of pop culture’s greatest stars: The Beatles and the Rolling Stones.

Wintour started her editorial career years before Vogue – in the fashion department of Harper’s & Queen in London. She moved from London to New York – from one publication to the next. In 1976, she took over as the fashion editor for Harper’s Bazaar in New York. Still in her 20’s, she left Harpers Bazaar to work for Viva where she became a high end editor and manager. Wintour continued on to work for Savvy and then New York magazine in 1981. Wintour was, and is, extremely dedicated to her style – she even had her own desk brought into her new office. “A contemporary Formica-topped affair on two metal sawhorses as legs…along with a high-tech chrome-framed chair with a seat and back made of bungee cords,” wrote Jerry Oppenheimer, in his 2005 unauthorised biography of Wintour, Front Row.

In 1984, she married South African psychiatrist David Shaffer and two years later she returned to London as chief editor of British Vogue.  Wintour stated “I want Vogue to be pacy, sharp, and sexy. I’m not interested in the super-rich or infinitely leisured. I want our readers to be energetic, executive women, with money of their own and a wide range of interests,” she told the London Daily Telegraph. “There is a new kind of woman out there. She’s interested in business and money. She doesn’t have time to shop anymore. She wants to know what and why and where and how.” Her modern way of thinking reflected not only in her writing but in the way she presented fashion too. 

Wintour is said to have ended the supermodel era – by placing celebrities rather than models on her covers. She is also famous for combining old with new: her debut cover in November 1988 included a 19-year-old Israeli model outfitted in a pair of $50 jeans and a $10,000 jewel-encrusted t-shirt.

Wintour’s critical nature earned her many nicknames which included “Nuclear Wintour” and “Wintour of Our Discontent.” She loved that her strict and opinionated personality resulted in nicknames – it motivated her to continue to change fashion and develop magazines. After leaving British Vogue, she started working for Home and Garden. Within her first year, Nuclear Wintour rejected $2 million worth of already-paid-for photos and articles for Home and Garden and changed it’s name to HG.

Many people complained, but her bosses at at Condé Nast didn’t seem to have a problem. Her salary of more than $200,000 and an annual allowance of $25,000 for clothes and other amenities kept her happy and above and beyond this, the magazine’s owners arranged for Concorde flights between New York and London so Wintour and her husband could be together.

In 1988, Wintour became editor-in-chief of Vogue. This allowed her to return to New York. Vogue had been at the forefront of fashion since the 1960’s and suddenly found itself trailing behind Elle. Over Wintour’s 3 decade reign – the magazine was revived. She is known for spending huge amounts of money on photographers and photoshoots and for her sometimes extremely lengthly issues: that reached up to 832 pages in length – the most ever for a monthly magazine.


Wintour is not afraid to stand up for what she believes in. She told Oprah directly that she would have to loose 20 pounds (9 Kilograms) before putting her on the front over of her magazine. In 2008, when Hillary Clinton hinted that Vogue would make her appear too feminine which would undermine her presidential ambitions – Wintour was not afraid to strike back. In the February issue of her magazine she wrote: “The notion that a contemporary woman must look mannish in order to be taken seriously as a seeker of power is frankly dismaying. This is America, not Saudi Arabia. It’s also 2008: Margaret Thatcher may have looked terrific in a blue power suit, but that was 20 years ago. I do think Americans have moved on from the power-suit mentality.”

With that amount of power: a strong personality is a must. She insists her employees look fashionable at the workplace and maintain a thin figure. After all, it is the greatest fashion magazine in the world. 

 “The Devil Wears Prada (2003)” was originally a fictionalised book – written by a former assistant of Wintour. The novel was eventually made into a film. In 2006, Wintour turned heads as she arrived at the premier wearing Prada.

‘Extra’ is the best word I could possibly think of to describe Anna Wintour. Everyone else is trying to work out the best handbag to wear with their outfit – meanwhile Wintour doesn’t even have a handbag. Two of her staff members (Andre Leon Talley and Hamish Bowles) job is to carry all of her bits and bobs around for her. When deciding on seats for fashion week – not only does the seat have to be in the front row (of course!) but it has to not have a view, or be able to be viewed by, specific rival editors.

Wintour has been divorced from her husband since 1999 and is currently living in New York with her longtime boyfriend, Shelby Bryan.

Whenever I think of fashion week – I think of Anna Wintour. She is always the woman who catches my eye in the photos of of the front row fashionistas.

Let me know what you think of Anna Wintour in the comments below!

Cass xx



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