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'Vogue's' Anna Wintour Criticizes Melania Trump's Style But Praises Michelle Obama And NYC's First Lady In New Interview: 'Think About The Women That One Admires'

April 9, 2026 by Abigail Connolly
shefinds | Celebrity
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It’s well known in the fashion world these days that Anna Wintour, the iconic former Vogue editor, has coveted opinions on celebrity style. Well, she recently weighed in on Melania Trump and Michelle Obama.

In a new interview for the famous fashion publication, the magazine tycoon opened up about First Lady fashion, particularly mentioning Melania Trump and Michelle Obama. Anna compared the two prominent women, giving subtle digs towards Melania’s style, while looking back and praising Michelle’s. Read more about what she had to say about the two women below.

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Anna Wintour Subtly Shades Melania Trump's Style In A New 'Vogue' Interview

When someone holds such a powerful position in the fashion world, like the editor of Vogue, people tend to want to hear as much about what they think of other celebrities as much as possible. Though she recently announced she's stepping down as the editor-in-chief at the magazine, Anna Wintour's opinions on today's fashion trends and the most stylish stars are still considered super valuable.

 

Recently, to promote the Met Gala and the premiere of The Devil Wears Prada 2, a film rumored to be inspired by her time at Vogue, the UK native sat down for an interview with the Miranda Preistly herself, Meryl Streep, and famous director Greta Gerwig. The pair spoke about the film, their experiences as women at the top of their fields, and more.

 

At one point, the conversation shifted into the style and fashion trends used by American first ladies, bringing up the current one, Melania, whose outfits and ensembles have been making headlines.

 

"Do you think about how women are meant to dress to communicate power?" asked Gerwig, to which Anna responded, "I don't think wearing a power suit to the office is in any way necessary."

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Anna Praises Michelle Obama As An Admirable Woman

After giving the subtle dig towards the Slovenian model's sense of style and her famous pantsuits, the 76-year-old shifted the conversation towards a former First Lady whose fashion sense she much more clearly approved of.

 

Anna began talking about Michelle Obama, who also made headlines during her days in the White House for her fashion choices, and continues to receive praise for her trendy looks. She even recently released a new book, The Look, which contains behind-the-scenes photos that detail her style transformation.

 

"Think about the women that one admires: Mrs. Obama comes to mind," explained Anna. "Whether she's wearing J.Crew or Duro Olowu or Matthieu Blazy's Chanel, she always looks like herself. I'm full of admiration for New York City's new first lady because she looks so cool and wears a lot of vintage, young, modern, and also entirely herself. To be fair, Melania Trump also always looks like herself when she dresses."

 

That's when the Oscar-winning actress, Meryl, chimed in, getting heated about a particular piece of clothing Melania once wore during her husband's first term.

 

"I think the most…powerful message that our current first lady sent was in the coat that said 'I Really Don't Care, Do U?' when she was going to see migrant children who were incarcerated," she admitted. "All dress is about expressing yourself, but we're also subject to larger historical and political sweeps of expectation."

Author:

Editorial Assistant

Abigail is a journalist based in Brooklyn, New York. As an Editorial Assistant for SheFinds, she covers topics ranging from celebrity news and fashion to wellness. She has written for other publications, including Chip Chick, Bandsintown, BroadwayWorld, and more. When she isn't writing, Abigail loves spending time in the city with her friends, being a 'dog mom' to her Chihuahua, and singing along to some of her favorite music.

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