Entertainmentabout 1 month ago4 min read

Harry Styles, Sabrina Carpenter and More of the Most Daring Grammy Awards Looks of All Time

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Harry Styles, Sabrina Carpenter and More of the Most Daring Grammy Awards Looks of All Time
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Why it matters

From Britney Spears’ blindly white gown to Miley Cyrus’ gold mesh dress at the Grammys, some stars hit all the right notes with their red carpet looks.

Key takeaways

  • Among the most daring looks came from Chappell Roan, whose 2003 Jean Paul Gautier spring/summer couture collection gown was worthy of any art museum.
  • The fashion moment was so iconic that Google Image Search was born.RihannaThe Fenty Beauty founder looked like a vision in white at the 2011 Grammys.
  • Inspired by Sandro Botticelli's "The Birth of Venus," this look was a work of art.The "Adore You" signer turned the 2023 Grammys red carpet into a rainbow paradise with a colorful sequined jumpsuit.

In fact, the “Manchild” singer proved she’s always had good taste when she stepped out at the 2025 Grammys in a daring powder blue JW Anderson backless dress featuring a pear-cut diamond pendant cascading down her back and an ostrich feather trim along the hem and hips.

Among the most daring looks came from Chappell Roan, whose 2003 Jean Paul Gautier spring/summer couture collection gown was worthy of any art museum. In fact, the blue-and-yellow look was literally imprinted with Edgar Degas' portrait of ballerinas on the skirt.

The "Pink Pony Club" singer—who is nominated for Record of the Year and Best Pop Solo Performance this year—completed her look with a feathered headpiece featured in the original runway show. Chappell's stylist Genesis Webb felt it was essential to have her client in archival couture. 

"Regardless of the designer, I wanted something with history; something that carried weight beyond aesthetics,” she told Vogue last February. "Gaultier had been on my mind for her for some time, so I reached out, and when this particular archival piece was presented, I had an immediate visceral reaction. It wasn't just an option, it was the dress. While I had several looks prepared for the fitting, this was the only one that truly aligned with the vision."

As the curtain slowly begins to rise on the 2026 Grammys, keep reading for more celebs who didn't need any luck, babe, when it came to red carpet fashion.

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Published: Jan 31, 2026

Read time: 4 min

Category: Entertainment