Anna Wintour – The Woman behind the Sunglasses

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/ published 3 years ago

Anna Wintour – The Woman behind the Sunglasses

While she has transformed the fashion world over and over again, her style remains a constant. For example, she wears her hair in a signature bob since she was 14

The world has been fascinated with Anna Wintour since she took over the position as editor in chief for Vogue in 1988. Whether it is her impenetrable sunglasses, her flawless style, or her antics, there is always something about Wintour that catches the eye. And while she has transformed the fashion world over and over again, her style remains a constant. For example, she wears her hair in a signature bob since she was 14. That being said, here are some interesting things about the woman behind the sunglasses.

A revolutionary from the get-go

Her first US Vogue cover was so different than the norm for the magazine, that printers asked her if it was a mistake. The cover featured Israeli model Michaela Bercu wearing Guess jeans and a Christian Lacroix Hatue Couture top (one featuring a cross made of jewels).


Wintour later recalled that nobody expected that picture to make it to the cover. The jacket was actually part of a suit, but the mode has gained weight and couldn’t fit into the skirt. So, Anna decided to run it with just the jacket and reinforce the playful idea she had. At the time, Vogue was running close-ups for the cover, and the new cover was revolutionary.

The new cover had everything different. Michaela wasn’t looking at you, she had her eyes almost closed, her hair was blowing across her face, and it looked easy and casual, like a moment snapped on the street. Wintour sensed the winds of change from the get-go, and that is what makes her so influential in the fashion world.

Woman in the long list of high school dropouts

We’ve heard a number of stories about successful men dropping out of college and high school and working on their idea. The list includes Steve Jobs, Bill Gates, and Mark Zuckerberg. But what about female dropouts that have launched a successful career?

Wintour dropped out of London Collegiate School and went to work at Harrod’s. She rebelled by flaunting the dress code, and she eventually dropped out.

Shoes to match her skin tone

Anna has had a “love affair” with Manolo Blahnik for more than 20 years. She always wears cross-front slingbacks with a delicate kitten-heel. The shoes are custom made for her, and they must match her skin tone. Apparently, the style is nicknamed “the AW”. When she has a suntan, the tone of the shoes matches her skin again.


Journalism in her blood

Journalism has always run in the Wintour family. Her father Charles was the editor of the London Evening Standard from 1959 to 1976. He founded the annual Evening Standard Theatre Awards, one that still runs today. Anna attends the awards every year. Rumor is, when she was young, her father consulted her on how to make the newspaper relevant to the youth of the era.

She has royalty in her blood

Anna has some royal blood in her. Lady Elizabeth Foster, the late 18th century novelist who was the Duchess of Devonshire is her great-great-grandmother. Sir Augustus Vere Foster, the last Baronet of that name, is her granduncle.


She was named a Dame in 2017 by the Queen. At the ceremony, Wintour briefly removed her signature sunglasses as she was entering the ballroom. She wore a custom Channel dress.

Her favorite sport is tennis

Anna has a strict daily routine and schedule. But with all work tasks, she always finds time to play her favorite sport, which is tennis. She plays tennis before work, and rises at 5am every day to get her daily dose. She is also a regular at the US Open, Wimbledon, and French Open tournament. Rumor is she has a soft spot for Roger Federer.

Supporter of the democrats

It is no secret that she is a democrat supporter. She has supported the Democratic Party since Hillary ran for Senate in 2004. She also supported John Kerry for president in 2004, Obama in 2008 and 2012, and Hillary in 2016. She has co-hosted several fundraisers for the Democratic Party. There were rumors that her support for Hillary would yield an ambassador role.

New York is her favorite city

Anna lives in New York, where the headquarters of the US Vogue is. But she loves the city, and she cites diversity as one of the reasons. According to Anna, New York is a “city for people who want to work. It is a city where everyone is from somewhere else, and you are not judged by your accent, who your dad was, or any other Englishness”.

Strict daily schedule

As mentioned previously, Vogue’s editor in chief has a strict daily schedule. She rises every morning at 5am, plays tennis, has her hair done by a stylist at her home, and then arrives at Vogue by 8am. She is in bed by 10:15pm every night. She limits her presence at parties at 20 minutes the most.

She has high standards for covers

The cover of Vogue is arguably one of the most prestigious covers not just in the fashion world, but in the magazine world overall. And she has high standards for celebrities appearing on the cover. For example, rumors are she told Oprah to lose weight before her photo shoot, and she also ordered Hillary not to wear a blue suit.

She doesn’t take selfies

In a world obsessed with selfies, Anna is one of the people that will never take a selfie. In a video in 2014 describing her daily work, the cameraman asked her to take a selfie at the end. She replied “I’ve never taken a selfie, and I don’t plan to start now”.

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