Anna Wintour Praises Michelle Obama and Melania Trump's Fashion, Yet Meryl Streep Objects

Vogue pulled one of the most iconic moves to date by putting its former editor-in-chief, Anna Wintour, and actress Meryl Streep on the cover of the magazine’s May 2026 issue. The duo posed for the cover story to promote the much-anticipated sequel to the 2006 movie The Devil Wears Prada.

Anna Wintour, whose leadership at Vogue turned the magazine into the cultural epicenter it is today, is widely believed to have inspired Meryl Streep’s Miranda Priestley, the domineering and revered chief editor of the fictional fashion magazine Runway in the movie.

During the interview, the two ladies shared their opinions on Melania Trump's fashion choices. Filmmaker Greta Gerwig was present during the interview. She asked the two Mirandas whether the phrase “dressing for success” applies to women as much as it does to men.

Gerwig asked, “The question of how you present yourself is so much what The Devil Wears Prada is about. For men, there’s a clear code: You dress for the job you want. But for women, dressing has always been more nebulous. Anna, how much do you think about that? Do you think about how women are meant to dress to communicate power?”

Wintour seems to believe women do not need power suits to convey authority. She did not try to hide her favoritism toward Michelle Obama and unapologetically praised her choice of outfits. However, she concluded her statement by complimenting Melania Trump for “looking like herself.”

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The former Vogue editor-in-chief said, “I don’t think wearing a power suit to the office is in any way necessary. Think about the women that one admires: Mrs. Obama comes to mind.”

She added, “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.”

However, Meryl Streep seemed to have a different opinion about the first lady’s fashion statement. She seized the opportunity to take a cheeky jibe at Melania Trump for not being mindful of what she wears. While she agrees that “all dress is about expressing yourself,” at the same time, she believes that women are “subject to larger historical and political sweeps of expectation.”

She said, “I have so many thoughts about this. 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.”

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Streep expressed her frustration at the fact that women, no matter how much power they hold, are made to believe they are less than men. “I’m stunned at how women in power have to have bare arms on television while men are covered in shirts and ties or a suit. There’s an apology built into women. They have to show their smallness.”