The Grammy Awards are the music world’s Met Gala. It's the biggest night in music, when grandiose entrances, memorable red carpet quotes, and dramatic outfit changes run rampant. Just take a look at the Grammys of seasons past: A few highlights that come to mind are Jennifer Lopez’s iconic Versace jungle gown (which literally sparked the birth of Google Images), Britney Spears's Old Hollywood-meets-Y2K glamour, and Rihanna’s bubblegum pink cupcake Giambattista Valli moment. No matter who's nominated or what their signature style is, our favorite music stars play no games when it comes to outfit choices for the highly anticipated awards show.
Coinciding with the 65th annual Grammy Awards— filled with even more dramatic glamour, spring beauty inspo, and luxe finishing touches—Byrdie is taking a look at some of the best Grammys looks of all time. Keep reading to look back at all the highlights and get excited for the rest of awards season.
One of the biggest style icons of the free-spirited '70s, Cher turned heads at the Grammys with a white bikini-style top and a holographic sequin butterfly brooch that matched her oversized hair clip.
Dolly Parton (1977)
Cowboy chic has definitely been trending over the years with memorable style moments from the likes of Kacey Musgraves and Lil Nas X, but it was Dolly Parton who made it part of her DNA. The star, nominated for best country vocal performance that year for her album All I Can Do, wowed in a Barbiecore-inspired cowgirl jumpsuit.
Paula Abdul (1990)
Paula Abdul embodied '80s prom meets New Year's Eve glamour with this glittering fringe dress by Bob Mackie, jumbo gold accessories, and simple metallic clutch. 1990 marked the artist's first ever Grammy nomination as well as her performance of "Straight Up," making for a night that altogether shone as bright as her outfit.
Mariah Carey (1991)
Mariah Carey was only 20 years old at her Grammy red carpet debut in 1991, where she took the Best New Artist award in a classic, form-fitting LBD. It was a simple yet impactful look to mark the start of her consistently impressive career.
En Vogue (1991)
Also in 1991, En Vogue honored the African diaspora in traditional, color- and print-filled looks that brightened the night almost as much as their impromptu "Boogie Woogie Bugle Boy" on-carpet performance.
Winning Best Mexican/Mexican-American Album in 1994, Selena graced the stage in a white, sequin-embellished Lillie Rubin gown with a classic silver halter strap. The night went down as one of the most triumphant moments in the queen of Tejano music's career.
Salt-N-Pepa and DJ Spinderella (1996)
Salt-N-Pepa and DJ Spinderella made us believe in power suits at the 1996 Grammys. In matching mint green suits and clear PVC handbags, the artists were way ahead of their time—we can imagine a look like this going viral today.
Erykah Badu (1999)
An R&B legend with as legendary style, Erykah Badu looked effortlessly cool in a leather patchwork gown (that she designed herself!) and her signature muted yellow Nefertiti head wrap.
Jennifer Lopez (2000)
It's hard to think of Grammys looks without J.Lo's plunging Versace gown coming to mind. The belly-button-baring dress was one of the most scandalous gowns on the carpet at the time, and it generated so much interest that Google had to create its image search function to help fans find it. The look is still just as iconic, especially after she closed Versace's Spring 2020 show in a recreation of the historic piece.
Britney Spears (2000)
Inspired by Marilyn Monroe, Britney Spears went full-on glam in this white Randolph Duke halter gown and Oscar de la Renta stole at the 2000 Grammy Awards, where she was nominated for Best New Artist and Best Female Pop Vocal Performance. Sleek, straight hair turned the throwback look into an iconic Y2K moment.
Destiny's Child (2001)
Destiny's Child proved that all good things come in threes in 2001. Designed by Beyoncé's mom, Tina Knowles, the shimmering green cutout gowns were the perfect complement to the two awards the trio took home for "Say My Name."
Sheryl Crow (2005)
Abs were the talk of the town at the 2005 Grammy Awards with Sheryl Crow's cutout yellow Roberto Cavalli gown. Slightly form-fitting, the dress's halter neckline and 3D gold embellishments provided elegant balance with the airy skirt.
Lady Gaga (2010)
Decked out in a celestial, high-low Armani Privé gown and bejeweled platform heels, Lady Gaga embodied unconventional glamour at the 2010 Grammys. The star raved to press that year that the creation aligned with her artistic spirit, and we couldn't agree more.
Nominated as one of the collaborators on "All of the Lights," which would take home two Grammys, Fergie showed out in an orange lace dress by Jean Paul Gaultier with ruffle sleeves and a small train. The see-through look, which she paired with dark undergarments, made a statement that felt tailor-made for a Hollywood red carpet.
Queen Bey looked bridal chic in this white form-fitting gown by Michael Costello. The sheer dress had beautiful floral lace details and negative space to show depth.
A veritable style icon, Rihanna can do no wrong. The musician and fashion/beauty entrepreneur turned heads in 2015 with this bubblegum pink Giambattista Valli gown. The cupcake-adjacent tulle and ruffles harmonize perfectly with the bright hue to make an unforgettable fashion moment.
Solange Knowles (2017)
A hair chameleon and fashion icon, Solange Knowles dressed to impress in a gold pleated Gucci gown at the 2017 Grammys, where she won her first award. The ruffle sleeve and tiered waist stood out against the high-slit silhouette, resembling the iconic Grammy trophy in the best way.
Miley Cyrus (2018)
Typically one to make a risky statement, Miley Cyrus stepped out in 2018 wearing a Zac Posen ballgown to prove that she can rock traditional glamour just as well. Subtle old Hollywood waves completed the stunning Grammys look.
Kylie Jenner (2019)
Regardless of whether you stay up to date on Kylie Jenner and her famous family, there's no denying that the star and beauty entrepreneur's baby pink Balmain jumpsuit was an unforgettable highlight of the 2019 Grammys. Pink was a big theme at the awards that year, and Jenner definitely answered the call in the form-fitting, structured look.
Cardi B (2019)
Just as much as she makes a splash with her music, Cardi B knows how to hold the world's attention on the red carpet. This vintage Mugler gown, inspired by an oyster with its architectural pink waist and pearl detailing, was a capital-F fashion moment that got everyone talking.
Jennifer Lopez (2019)
In 2019, J.Lo created another iconic Grammys memory in a straight-off-the-runway Ralph & Russo gown, featuring a crystal-embellished neckline and a matching wide-brimmed hat.
Ariana Grande (2020)
Ariana Grande and her 20-foot-wide, custom Giambattista Valli gown were all I could think about at the 2020 Grammy Awards. Fit for a princess, the silver-gray tulle masterpiece had cloud-like tiers and ruffles perfect for posing and twirling the night away.
Translating Britney Spears's Y2K statement to a new generation, Lizzo was the epitome of Old Hollywood glamour in a custom Versace gown. The elegant design featured modern structural details, which when paired with a stole and classic jewelry felt like the perfect degree of boldness.
Doja Cat (2021)
Doja Cat showed off the power of a plunging neckline with this low-cut, feathered Roberto Cavalli gown. The show-stopping cream and black bikercore top featured gold zippers and embellishment, which cascaded into the billowing neon-green-and-black feathered skirt.
Dua Lipa (2021)
Nominated for six awards that year, Dua Lipa dazzled the 2021 Grammys red carpet in a sparkling sheer Versace gown with baby pink undergarments. Covered in Swarovski crystals, the dress seemed to take inspiration from Cher's 1974 butterfly look.