Style-wise, the Grammys stand out from the rest of the award shows. Whereas Hollywood’s finest like to play it semi-safe at the Oscars and the Golden Globes, choosing pretty gowns and the occasional suit, those who attend music’s biggest night of the year rarely follow suit, with grandiose entrances and outfit changes a common occurrence. That’s how we ended up with such a wide array of daring looks from Grammys past, including J.Lo’s iconic Versace jungle gown, Cardi B’s Mugler oyster masterpiece and Rihanna’s bubblegum pink Giambattista Valli meme dress.
While, of course, we tune in to the Grammys each and every year for the performances and awards, like the hotly contested Album of the Year and Best New Artist, we also can’t help but have fashion be a main focus of the night. With the 66th Annual Grammy Awards behind us, we thought we’d take a trip down memory lane. Join in as we count off our all-time best-dressed looks from music's biggest night, including a couple of favorites from the 2024 Grammys.
This article was originally published in March 2020 and has since been updated.