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Anna Wintour: Pics of the ‘Vogue’ Editor-in-Chief Over the Years

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June 26, 2025 3:25PM EDT
Anna Wintour: Pics of the 'Vogue' Editor-in-Chief Over the Years
Kevin Mazur/Getty Images for The Met Museum/Vogue

Anna Wintour, longtime editor-in-chief of ‘Vogue,’ is stepping down after 37 years. See photos of her most iconic moments and signature style through the decades.

Anna Wintour has been a defining force in fashion for nearly four decades. Appointed editor-in-chief of Vogue in 1988, she transformed the magazine into a global authority on style, championed emerging designers, and turned the Met Gala into fashion’s biggest night. Known for her signature bob, dark sunglasses, and sharp eye for trends, Wintour’s influence extended far beyond the pages of Vogue.

In June 2025, Wintour announced she would be stepping down as Vogue’s U.S. editor-in-chief while continuing in her broader role as Condé Nast’s global chief content officer. As she enters a new chapter, we’re looking back at her most memorable fashion moments—from front-row appearances at Fashion Week to red carpet arrivals at the Met Gala.

Scroll through the gallery to see Anna Wintour’s iconic style evolution.

1 of 10

Anna Wintour during Milan Fashion Week

Anna Wintour during Milan Fashion Week
Grosescu Alberto Mihai/Shutterst

Anna Wintour smiles during Milan Fashion Week in Italy on Feb. 21, 2020. She wore a black, gray and white checkered jacket and sunglasses. 

Anna is best known as the longtime edior-in-chief of ‘Vogue’ magazine, one of the most famous fashion-based magazines in the world. She started the position in 1988 and is known all over the world for her signature bob hairstyle and sunglasses. 

She is from London, England and her father, Charles Wintour, was the editor of the ‘Evening Standard’ so she came from a family that had magazine/newspaper industry experience. She went to North London Collegiate School and eventually moved to New York City, when she became a juniro fashion editor for ‘Haper’s Bazaar’ in 1975. She then started working for ‘Vogue’ in 1983 before earning her huge job as the editor.

Since she became editor at ‘Vogue’ she has been involved in many fashion-related events such as fashion shows and other industry-related events. She has worked with many of the top models in the world and oversees who is featured on the cover of each ‘Vogue’ issue.

April 13, 2020, 4:43PM
2 of 10

Anna Wintour In New York

Anna Wintour In New York
Gregory Pace/Shutterstock

Anna Wintour rocked all black to the opening of ‘Plaza Suite’ on Broadway in March 2022. The editor sported shades on the red carpet.

April 26, 2022, 10:03AM
3 of 10

Bee Shaffer & Anna Wintour At The Tony Awards

Bee Shaffer & Anna Wintour At The Tony Awards
Gregory Pace/Shutterstock

Bee Shaffer and Anna Wintour smiled side-by-side at the 73rd Annual Tony Awards. Bee sported a silver gown, while her mom rocked a green dress with flowery-designs.

April 26, 2022, 10:03AM
4 of 10

Charles & Elizabeth Shaffer At The Met Gala

Charles & Elizabeth Shaffer At The Met Gala
Rob Latour/Shutterstock

Anna Wintour’s son Charles Shaffer and his wife Elizabeth Shaffer stunned at the 2017 Met Gala. They both matched in dark, navy blue outfits.

April 26, 2022, 10:03AM
5 of 10

Anna Wintour at the CFDA Fashion Awards

Anna Wintour at the CFDA Fashion Awards
Erik Pendzich/Shutterstock

Anna Wintour at the CFDA Fashion Awards at the Brooklyn Museum in New York. She wore an Alexander McQueen dress to the event.

April 13, 2020, 4:43PM
6 of 10

Anna Wintour posing for photos

Anna Wintour posing for photos
Stephen Lovekin/Shutterstock

Anna Wintour posing at the CFDA Fashion Awards in June 2019. She gave a slight smile to cameras. 

April 13, 2020, 4:43PM
7 of 10

Anna Wintour at the Costume Institute Benefit

Anna Wintour at the Costume Institute Benefit
Charles Sykes/Invision/AP/Shutte

Anna Wintour attends The Metropolitan Museum of Art’s Costume Institute benefit gala celebrating the opening of the ‘Camp: Notes on Fashion’ exhibition, in New York in May 2019. She wore a pink feathery look.

April 13, 2020, 4:43PM
8 of 10

Anna Wintour at the Met Gala

Anna Wintour at the Met Gala
Clint Spaulding/Shutterstock

Anna Wintour smiles at the Met Gala in New York City. She wore a flattering pink outfit.

April 13, 2020, 4:43PM
9 of 10

Anna Wintour at the Dries Van Noten show

Anna Wintour at the Dries Van Noten show
Shutterstock

Anna Wintour at the Dries Van Noten show during Paris Fashion Week in France in Feb. 2019. She wore a long blue coat over a blue and white dress.

April 13, 2020, 4:43PM
10 of 10

Anna Wintour during Paris Fashion Week 2019

Anna Wintour during Paris Fashion Week 2019
Shutterstock

Anna Wintour walking during Paris Fashion Week in 2019. She was a sight in blue.

April 13, 2020, 4:43PM