The Worst Dressed Stars 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? 

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.

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. 

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. 

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