Anna Wintour at Met Gala: Dresses Through the Years

By:

Medina Lynn, Vivian

June 26, 2025 4:28PM EDT

As Anna Wintour steps down from ‘Vogue,’ revisit her most iconic Met Gala looks. See how her signature style has evolved on fashion’s biggest night.

For over two decades, Anna Wintour has been the first to arrive at the Met Gala—and the one who sets the tone for the night. As the longtime editor-in-chief of Vogue and co-chair of the annual event, she’s delivered a steady stream of elegant, tailored, and often custom Chanel looks that reflect her signature style.

Now, as Wintour steps down from her role at Vogue after 37 years, we’re looking back at her unforgettable Met Gala fashion moments. From her debut at the event in the 1990s to her most recent appearances, these photos chart the evolution of one of fashion’s most iconic figures on one of the world’s most glamorous red carpets.

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — Anna Wintour stuns in a flowery- white dress for the 2021 Met Gala. The dress was covered in a wide-array of colors for the special event.

Anna Wintour has been a fashion icon for over 30 years. She’s most notably been an editor at ‘Vogue’ since 1985, and she became the editor-in-chief of the magazine in 1988. With her longstanding position at ‘Vogue,’ it should come as no surprise that she’s been a regular guest at the Costume Institute Benefit at New York’s Metropolitan Museum of Art (better known as the Met Gala) for years. The event is widely considered one of the biggest nights in fashion, so of course, Anna has been a regular for decades. Not only does she attend, she also regularly stuns in a wide-array of outfits, showing off her keen eye for fashion.

Scroll through our gallery to check out photos of Anna Wintour’s Met Gala looks through the years.

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Anna Wintour at the 2023 Met Gala

Anna Wintour at the 2023 Met Gala — Anna Wintour wears a gorgeous dress to the 2023 Met Gala in New York City on May 1. She arrived at the event with her rumored new boyfriend, actor Bill Nighy.

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — Anna Wintour sported a bright pink look for the 2019 Met Gala, themed ‘Came: Notes on Fashion.’ The pink dress glittered under a fluffy feathered top.

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — Anna Wintour sported a white dress for the 2018 Met Gala. The dress also had a silver cross on it for the theme ‘Heavenly Bodies: Fashion and the Catholic Imagination.’

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — The 2017 Costume Institute Benefit at The Metropolitan Museum of Art (REX/Shutterstock)

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — The 2016 Costume Institute Benefit at The Metropolitan Museum of Art (REX/Shutterstock)

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — The 2015 Costume Institute Benefit at The Metropolitan Museum of Art (REX/Shutterstock)

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — The 2014 Costume Institute Benefit at The Metropolitan Museum of Art (REX/Shutterstock)

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — The 2013 Costume Institute Benefit at The Metropolitan Museum of Art (REX/Shutterstock)

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — The 2012 Costume Institute Benefit at The Metropolitan Museum of Art (REX/Shutterstock)

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — The 2011 Costume Institute Benefit at The Metropolitan Museum of Art (REX/Shutterstock)

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — The 2010 Costume Institute Benefit at The Metropolitan Museum of Art (REX/Shutterstock)

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — The 2009 Costume Institute Benefit at The Metropolitan Museum of Art (REX/Shutterstock)

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — The 2008 Costume Institute Benefit at The Metropolitan Museum of Art (REX/Shutterstock)

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — The 2007 Costume Institute Benefit at The Metropolitan Museum of Art (REX/Shutterstock)

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — The 2006 Costume Institute Benefit at The Metropolitan Museum of Art (REX/Shutterstock)

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — The 2005 Costume Institute Benefit at The Metropolitan Museum of Art (REX/Shutterstock)

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — The 2004 Costume Institute Benefit at The Metropolitan Museum of Art (REX/Shutterstock)

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — The 2003 Costume Institute Benefit at The Metropolitan Museum of Art (REX/Shutterstock)

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — The 2001 Costume Institute Benefit at The Metropolitan Museum of Art (REX/Shutterstock)

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — The 1999 Costume Institute Benefit at The Metropolitan Museum of Art (REX/Shutterstock)

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — The 1993 Costume Institute Benefit at The Metropolitan Museum of Art (REX/Shutterstock)

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Anna Wintour — Throughout The Years At The MET Gala

Anna Wintour — Throughout The Years At The MET Gala — The 1990 Costume Institute Benefit at The Metropolitan Museum of Art (REX/Shutterstock)

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