The Worst Red Carpet Misses in Grammys History

The Grammys are the most risk-taking of red carpets, and that’s why fans love it. However, as everyone knows, not every risk pays off. So who are some of the standouts in the worst of all time on the Grammys red carpet?

Memorable flops include Shania Twain in 2023, in this polka dot trippy “Alice in Wonderland”-esque suit with red hair. It’s deliciously wild, yes, but it leaves us wondering what pray tell is inside that top hat?

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Harry Styles is beloved for his fashion risks, and the skin-baring rainbow jumpsuit he wore to last year’s Grammys was part of a moment for the singer to push boundaries on the red carpet. But when isolated, the look comes across as more pure Halloween.

Speaking of the October holiday, Annie Lennox in a black latex Mini Mouse S&M dress — plus ears — would get a nomination at a costume competition, but she definitely didn’t win any fashion awards. And in 2024, Montaigne opted for avant-garde fashion in a theatrical ensemble featuring a ruffled collar, ombré-dyed white blouse and layered shorts over printed tights. The look incorporated gothic and Victorian influences, highlighted by a star-shaped necklace and red cowboy boots.

A full fashion mess belongs to Pink with her 2002 asymmetrical look. The one-leg pant and the furry garter together with the skinny bow tie is sad and beyond explanation. Alicia Keys in 2002 is another example of a getting-dressed-in-the-dark moment. The jeans and tank top layered with floral embroidered sheer hood and DIY sarong are one of the leading moments of this list — not a good thing, obviously.  2024 brought Ice Spice in a two-piece set by Kimora Lee Simmons’ brand Baby Phat, with fur-trimmed details. The form-fitting outfit featured a jacket clasped together, thigh-high slit on the skirt, intricate stitching and a baby phat logo belt in the front. She accessorized with a cross necklace, gold heels and her signature curly ginger hair.

And sometimes, fit is the biggest offender, as seen on Kylie Jenner in 2019 and Justin Bieber in 2022. Oversize can be cool or it can be the ultimate error.

Below see more of the Grammys red carpet outfits that missed.

Grammys Biggest Red Carpet Misses of of All Time [PHOTOS]

Launch Gallery: Grammys Biggest Red Carpet Misses of of All Time [PHOTOS]

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