Style-wise, the Grammys stand out from the rest of the award shows. Whereas Hollywood’s finest like to play it 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.
With the 66th Annual Grammy Awards airing, 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.