The Best Dressed Stars in Grammys History

The Grammy Awards return Sunday, this year held in Los Angeles, and with them come one of the boldest red carpets in all of celebrity land. 

Easily the best Grammys fashion moment of all time is Jennifer Lopez, whose green Versace cleavage-baring dress at the 2000 Grammy Awards was so attention-grabbing it was the launch of Google Images. It’s going to take a long time — and a big effort — for anyone to match that moment. 

Other best dressed moments in Grammys history include Lady Gaga, no stranger to a best-dressed list, in Armani at the 2010 awards. Cardi B earned her spot in fashion history at the 2019 ceremony, when she arrived in a vintage Mugler look that was ahead of the current red carpet trend of vintage dressing. Cher’s 1974 look, a white butterfly bikini top and matching hair clip, is best-dressed worthy, as is the matching white looks from Janet Jackson and Michael Jackson at the 1993 Grammys.

The best moment from the 1990s has to be Chili, Lisa “Left Eye” Lopes and T-Boz of TLC at the 1996 awards in dressed-up versions of cargo pants and bra tops. Other all-white winners include Shania Twain’s high-neck gown in 1999, exuding that era’s minimalism trend. 

Britney Spears’ 2000 white, formfitting tank dress and fur shrug, with a bit of bling, was her own take on old Hollywood glamour, and it was one of her best looks. Cyndi Lauper at the 1984 Grammys proved original style always pays off, as did Lizzo as recently as last year, in a floral explosion of a Dolce & Gabbana look.