This weekend, the 66th annual Grammy Awards will take place in Los Angeles, California, and music’s top acts—Billie Eilish, Dua Lipa, SZA, Olivia Rodrigo, and more—are all set to perform. Of course, we’re very much looking forward to the star-studded red carpet. The Grammys have a history of delivering memorable style moments, à la Dua Lipa transforming into Donatella Versace circa 2022 and Cardi B emerging from a couture Mugler clam shell back in 2019.
Looking back on Grammys carpets over the decades, however, we can’t help but feel nostalgic for the days when the fashion was truly wild. We mean the simpler times, especially the ‘90s and early aughts, when some celebrities didn’t even have stylists. There was so much spontaneity and risk-taking, with celebrities conjuring up out-of-the-box inspiration and running with it—no matter how outlandish. Big-budget brand deals and sponsorships were essentially nonexistent; If a star saw something they liked, they just wore it and hope for the best.
Take Jennifer Lopez and her viral plunging Versace gown in 2000—a dress so good that it literally gave birth to Google Images. It’s a moment in fashion history that’s still talked about today, though Lopez wasn’t the first person to wear the design. In her Vogue video revisiting the look’s origin story, Lopez remembers that “Donatella had worn [the dress], one of the Spice Girls [Geri Halliwell] had worn it, and Sandra Bullock had worn it in another color.” Yet Lopez still felt the look was it; she was sure she could make it her own, and she did. Today’s crop of It girls would never step on the red carpet in an outfit already worn by a fellow performer; they’d sooner skip the Grammys altogether.
Another thing that made the Grammys of yesteryear so fun to watch? A total disregard for trends. In 1996, for example, Mary J. Blige sported a head-to-toe leopard ensemble by Dolce & Gabbana. “I was trying to do something new and different,” Blige told Vogue of the daring look. In 2002, Lil Kim donned a red leather (and bejeweled) Chanel moto suit—complete with a Chanel biker helmet to match. These were hardly ploys to land on Best Dressed lists; Stars were just having fun.
None of this is to say that the recent Grammys haven’t been a thrill to watch. Lady Gaga showed up in a Hussein Chalayan vessel in 2011, and I’m still obsessed with Harry Styles’s pink Gucci boa from 2021. But as a whole, recent Grammys fashion has been much more contrived, and less about disrupting the norm. Consider this our plea to bring back some Grammys fashion chaos this weekend. Doja Cat, Lana Del Rey, Billie Eilish—we’re looking at you.
Below, even more of the best Grammys looks over the year.