Every year stars gather for the annual Grammy Awards and the biggest night of music. It’s also when fashion comes out in full force. Remember Pharrell’s giant hat and Adidas look ? Ariana Grande’s Cinderella gown? Or how about Cardi B’s vintage Mugler human-sized clam shell dress? Black tie rules don’t apply, making for some of the most memorable fashion moments in award show history.
With that in mind, we rounded up the most iconic Grammy looks of all time .
An icon in her own right, Cher’s look from 1974 made butterflies look like the ultimate accessory.
The 90s were the era of girl groups and TLC were the frontrunners for many reasons. Their coordinated all-white outfits at the 1996 Grammys were the perfect combination of sexy, cool, and oh-so ‘90s.
Aaron Carter 1999
A mini-heartthrob from the 2000s, Aaron Carter walked the red carpet in a yellow suit but it was his iced-out custom nameplate chain that made the look.
Brandy and Monica 1999
This 90s duo coordinated cream-colored outfits for their Grammy red carpet looks before winning the award for Best R&B Performance by a duo, we stan.
Britney Spears 2000
This has to go down in history as one of Britney’s best red carpet looks. The Princess of Pop wore a chic Randolph Duke white gown and Oscar de la Renta fur throw for her Grammy’s debut. Major Marilyn Monroe vibes.
J Lo and P Diddy 2000
THE Versace dress that led to the creation of Google Images. Really. The plunging V-neck dress is even more iconic than J Lo and P Diddy’s relationship.
Ciara turned heads in an Alexandre Vauthier Couture slip dress that had the highest thigh-slit of all-time. She pulled it off effortlessly.
Selena Gomez and Taylor Swift 2016
The ultimate BFF duo of the time. Selena wore a Calvin Klein mermaid dress, while Taylor brought the color and toned midriff in Versace.
Queen Bey has so many good Grammy looks but this all-black outfit by Nicolas Jebran is one of her best. From the hat to the sunglasses and slits, everything is perfect.
Miley Cyrus 2018
Miley showed up to the red carpet looking like a real-life princess in a tulle Zac Posen gown.
Lady Gaga 2018
You can always count on Lady Gaga for a stand-out look and this Victorian-esque Armani Privé gown burned into our minds forever.
Cardi B 2019
Cardi B had a Mugler Couture oyster moment on the red carpet where she was a human pearl and it was one of the most talked-about looks from that year.
Saweetie and Quavo 2020
One of hip-hop’s it-couples stole the show on the red carpet. Saweetie wore a bedazzled Moschino dress that paired perfectly with Quavo’s all-red satin Prada suit.
Shawn Mendes 2020
Shawn Mendes sent fans into cardiac arrest in a dapper red Louis Vuitton suit.
Ariana Grande 2020
Ariana Grande had a Cinderella moment in her Giambattista Valli ball gown that paired perfectly with her signature high-pony.
Lil Nas X 2020
Lil Nas X’s western-inspired Versace suit redefined cowboy style in a hot-pink instant.
Billy Porter 2020
Billy Porter killed it in a monotone blue for his red carpet Baja East look with LOTS of jewels. His hat even had a jeweled brim that opened and closed on demand. *Mic drop.