Anna Wintour's Unfiltered Thoughts On First Lady Fashion

Political fashion sometimes has a reputation for being boring, with a traditional emphasis on formality, rather than creativity. For First Ladies who don't hold an official elected office but are nonetheless political figures, that can mean walking a tricky fashion line. They need to look distinctive and recognizable without looking too avant-garde, which can be a tough balance to strike. Over the years, there have been plenty of outdated First Lady outfits that totally missed the mark.

Anna Wintour, the infamous long-time editor of "Vogue," is known for her discerning taste in fashion, and she prefers when First Ladies embrace a little self-expression. "Think about the women that one admires: [Michelle] Obama comes to mind," she revealed to Vogue in 2026. "Whether she's wearing J.Crew or Duro Olowu or Matthieu Blazy's Chanel, she always looks like herself."

Wintour doesn't believe that the First Lady needs to constrain herself to suits. She added that she is also a fan of First Lady of New York Rama Duwaji's stunning style. "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 and modern and also entirely herself."

It wasn't the first time Anna Wintour made a point of complimenting former First Lady Michelle Obama's taste in fashion. In 2019, Wintour appeared on The Economist's podcast, where she explained how Obama nailed First Lady style. "I think First Lady Michelle Obama really was so incredible in every decision she made about fashion," she explained. "She supported young American designers. She supported designers, indeed, from all over the world" [via Yahoo].

During her years in the White House, Obama was known for putting her own spin on political fashion. She championed newer designers, like Thakoon and Maria Pinto, and often reinvigorated the traditional sheath dress with bright colors and interesting patterns. Obama takes plenty of big fashion risks, and her decision to buck some First Lady style conventions was strategic, like when she turned to up-and-comer Jason Wu for her 2008 Inauguration Ball gown. "Big-name designers tended to dress the first lady for Inauguration," she told Vogue in 2025. "I was pretty clear that I wanted to change that up."