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Most Shocking Grammy Awards Red Carpet Looks of All Time

The Grammy Awards are fast approaching, and there’s one part of the evening we’re especially looking forward to, the stars debuting their red carpet looks. While the Oscars may have the most glamorous red carpet displays, the Grammys are a night for fashion risk-takers to shine, resulting in some seriously crazy looks. From Jennifer Lopez’s plunging Versace dress to Nicki Minaj’s papal regalia, we’re taking a look back at the most shocking Grammys red carpet looks ever — until this year, that is.

Celebrities always tend to go all out for a red carpet, and by all out, we’re not talking the most beautiful dresses but looks that made our jaws drop. The Grammys are more about performance and creativity than the oh-so-formal-look-your-best approach, stars take the opportunity to push boundaries on this very special musical night. They ask daring questions with their fashion choices, like: How much skin can I show before I am technically naked? And: What if an oyster turned into a dress?

As we look forward to the undoubtedly crazy looks the 2020 Grammys red carpet will bring, we can’t help but be nostalgic for these red carpet looks of days gone by. The ’90s were an exciting time of ever-lower necklines, lace-up detail, and an alarming amount of crochet — and we wouldn’t change a thing. Many of the looks featured here are worn by stars known, in their day-to-day lives, as fashion icons. And that’s part of why it’s so fun to see moments when they loosened up and really went there for a look. Whether or not they stuck the landing, we love them for it. And we’ll never forget the things they’ve done in the name of fashion.

Ready for this ride down memory lane? Click through — you won’t regret it.

This story was originally published in January 2020.

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