The Grammy Awards red carpet has always been the most fun and risk-taking stage of award season. Long before red carpets became hyper managed brand exercises, the Grammys encouraged boldness, experimentation and personality. Some of the true cornerstones of its fearless fashion history range from Cher and Lady Gaga to Grace Jones and Cardi B, just to name a few.
Cher set the tone in the 1970s, using the carpet as a platform for cultural conversation, famously wearing barely-there dresses designed by her longtime friend and collaborator Bob Mackie. In the ’80s, Grace Jones turned it into performance art, in sculptural leather and an exaggerated hat no less. Lady Gaga made her mark with unforgettable moments: at the 2010 Grammys she wore Space Age Armani Privé layered with crystal and origami‑inspired couture, and in 2011 she arrived inside a giant egg before "hatching" into latex - theatrical and very "Mother Monster."
Jennifer Lopez's green Versace dress in 2000 changed how celebrity, fashion and the internet collide. In 2001, Destiny's Child arrived in matching gold looks by Versace, showing how coordinated group dressing can be sexy, pushing the group’s branding to a whole new level. Nearly two decades later, Cardi B reinforced the Grammys' appetite for fashion theater in vintage Mugler couture, pearls and a dramatic sculptural silhouette at the 2019 award show - raising the bar to one where fashion knowledge and vintage dressing is a key part of the equation. These moments showed how the red carpet always rewarded boldness, personality and risk.
What makes someone best dressed at the Grammys is not elegance or polish. Unlike other awards shows, this carpet is all about self-expression and individuality. The best looks have personality, a strong sense of self, and a clear connection to the artist, their music or even an album mood board. Drama and performative energy is rewarded but execution still matters. A messy, ill-fitting or poorly made outfit can sink even the greatest idea. At fashion shows, insiders often code a look or collection as "very Grammys red carpet," because the concept, identity and meaning are already baked into the fashion.
What falls under worst dressed are usually outfits that lack authenticity. If it looks like the artist is playing dress up instead of expressing their creative selves, it most often fails. Safe, generic or overworked ensembles flop, and boldness without skill is just drama for drama's sake. Today's audience is way more knowledgeable and in-tune than ever and can spot a bad outfit a mile away.