The Best Looks From Grammy Awards Past

Jennifer Lopez in Versace, 2000

Do we even have to say anything?

This dress has a fan base. This dress and J-Lo in this dress are the very definition of a pop culture moment. It even became Google’s most-searched term at the time, prompting the birth of Google Images, according to then CEO, Eric Schmidt.

“People wanted more than just text,” he writes for Project Syndicate. “But we had no surefire way of getting users exactly what they wanted: JLo wearing that dress. Google Image Search was born.”

Beyoncé in Michael Costello, 2014

According to reporting by the Los Angeles Times, designer Michael Costello had no idea that Beyoncé would choose his gown.

“It’s Beyonce, so I feel like she has all these wonderful options made out of fairy dust. She has everything at her fingertips,” Costello says. “But she chose my dress, which I will be showcasing on the runway at New York Fashion Week on Feb. 8.”

Unbelievably, the gown was made in roughly a day.

“The dress is entirely handmade,” Costello explains. “I wanted to make it something that would stand out, and be extra special. So I added this nude mesh overlay to the fabric to give it the illusion of skin. I like that it has the feeling of flowers and leaves falling from a winter wonderland onto the nude-illusion fabric.”

Cardi B in vintage Mugler, 2019

This Venus-inspired gown is one of the most visually stunning moments in red carpet history, and it all came to be thanks to Cardi B’s stylist, Kollin Carter. Working months in advance of the show, Carter always had his eye on the black velvet, pink satin gown.

“From the moment I saw it, I knew it was going to be a debatable moment,” Carter tells WWD. “Some people would love it and some people would hate it and that’s everything we’re about when it comes to fashion. It’s meant to create a conversation.”

Archive gowns are notoriously difficult to get for events and red carpets. In fact, Cardi B was only the second person in 25 years that Mugler allowed to wear an archived piece. The first was Beyoncé in 2009.

Ariana Grande in Giambattista Valli, 2020

This Cinderella gown is definitely a fairy tale, and Grande’s signature blonde ponytail only completes the look. The huge grey tulle design required over 400 yards of fabric and 200 hours of work to create, according to the fashion house.

But it wasn’t long before the singer was out of this gown and into another grey statement-making piece.

“I’m so lucky. I had two very special custom looks made. And I couldn’t decide! This one is Schiaparelli. I was indecisive so I decided to do it twice. Which is really huge progress for me, because usually I cannot come within three feet of a red carpet without having a nervous breakdown,” she explained on the carpet.

Lada Gaga in Armani Privé, 2022

Known for her pushing the boundaries constantly in fashion, this look was a moment of true elegance and luxury for Lady Gaga. Up for five Grammy’s for Love for sale, her collaborative album with Tony Bennett, Gaga stunned in this Armani Privé black and white gown with a sculpted updo.

Gaga and Bennett, who passed in July of 2023, were friends for over a decade.

“I’ll never forget that today he could track every word I was saying and understood the world was celebrating him and celebrating jazz—a genre that embodies the joy, abundance and imagination of Black music throughout history,” she wrote in a Nov. 23 Instagram post. “This album happened because it was Tony’s idea and I made him a promise that we would make it and we did.”

Lil Nas X in Versace, 2020

Riding high on the success of Old Town Road, this hot pink Versace look fused western with something creative and flamboyant. Lil Nas X told CR Men at the time that the look was appealing to him because it took a risk.

“I’ve been trying to deviate from the norm that most guys wear—suit, tie… So when I saw the [Grammys] look, even as a sketch, I was like, ‘that’s crazy. That’s a talking point.’ I want to get more in tune with that flamboyant side as well. It’s an ongoing journey.”