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

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.

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Anna Wintour during Milan Fashion Week

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Anna Wintour In New York

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Bee Shaffer & Anna Wintour At The Tony Awards

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Charles & Elizabeth Shaffer At The Met Gala

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Anna Wintour at the CFDA Fashion Awards

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Anna Wintour posing for photos

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Anna Wintour at the Costume Institute Benefit

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Anna Wintour at the Met Gala

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Anna Wintour at the Dries Van Noten show

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Anna Wintour during Paris Fashion Week 2019

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