The 10 Most Iconic Grammys Style Moments of All Time, Ranked

Year: 1996

Mary J Blige has delivered incredible outfits her entire career. There may be none better than this bold animal print look from the 1996 Grammys. Her leopard print jumpsuit, matching shawl, big black shades, and platinum blonde hair would still turn heads. She also took home two trophies that night, which makes the exotic ensemble that much more iconic. –Mike DeStefano

Year: 2002

If you saw Lil Kim in the late ’90s and 2000s, chances are you saw Chanel’s double Cs on her. Styled by Misa Hylton, Kim became an unofficial face of the brand and helped bridge the gap between the French luxury house and the hip-hop world. This sporty all-red Chanel look featured a cropped moto jacket, leather pants, sporty shades, and heels. Kim even fully committed to the biker inspo by carrying a Chanel motorcycle helmet. These types of unconventional looks are why many still consider her the best-dressed female rapper of all time. –Mike DeStefano

Year: 2020

Tyler has never been shy about committing to a character. Whether it’s rocking a blonde bob wig and pastel suits for Igor or a Rwandan Amasunzu hairstyle and mask for Chromakopia, his style is always a major piece of his storytelling. Tyler has also created some memorable moments on the Grammys red carpet. Our favorite was in 2020 when he looked like he was ripped straight out of The Grand Budapest Hotel. The pink bellhop outfit with red accents was a great way to hint at the travel theme of 2021’s Call Me If You Get Lost. The fact that he was carrying around a suitcase packed with a striped polo, pleated pants, and an iced-out Igor chain that he would change into later that night was the perfect finishing touch. The look was so good that he even immortalized it with an Alex Moss chain. –Mike DeStefano

Year:2019

At the 2019 Grammy Awards, Cardi B made an unforgettable entrance in a vintage Thierry Mugler couture gown from the brand’s Fall 1995 collection. The design, which had not been seen in over two decades, featured a sleek black velvet sheath with a dramatic pink satin lining. The dress created an illusion of a clam shell that resembled Botticelli’s The Birth of Venus. Styled by Kollin Carter, this tribute to Mugler not only celebrated the designer’s legacy, but also cemented Cardi’s status as a fashion icon. –Shinnie Park

Year: 1984

Michael Jackson made history in 1984 when he won eight Grammys in one night. He wore a blue military jacket covered in shimmering rhinestones and adorned with golden epaulets created by his longtime costume designers Michael Bush and Dennis Tompkins. He kept up the glitz with accessories like sequined socks and the legendary bedazzled glove. The King of Pop’s fit was then immortalized with its own doll. –Mike DeStefano

Year: 2003

Eminem made a statement with his T-shirt when he hit the stage to perform his massive single “Lose Yourself” at the 2003 Grammys. He wore a grey tee with “Free Yayo” printed across the chest. G-Unit rapper Tony Yayo was behind bars, and the biggest rapper in the world at the time chose to show support on a national stage. Yayo speaks fondly of the gesture to this day. During a 2022 interview with DJ Vlad, he said, “I’m always gonna show him respect and love and salute him.” –Mike DeStefano

Year: 2003

Dipset didn’t adhere to the typical suit-and-tie award show dress code back in 2003. Instead, Juelz Santana, Cam’ron, and Jim Jones pulled up in colorful outerwear that had them looking like the flyest Power Rangers ever. Juelz rocked an ice blue mink and a matching NBA logo fitted with a bandana poking out from both sides. Killa Cam was decked out in his signature hue, baby pink. He wore a Jeff Hamilton jacket covered in NBA logos, a pink beanie, and even accessorized with a pink flip phone. Jim Jones’ fit was highlighted by a fire engine red Pelle Pelle. Of course, they all had a diamond-encrusted Dipset eagle chain hanging from their necks. This photo is the definition of 2000s hip-hop fashion. –Mike DeStefano

Year: 2000

Jennifer Lopez’s 2000 Grammy look in that green Versace dress is a moment that still echoes in the fashion world. The silk chiffon gown, with its jungle print, plunging neckline, and thigh-high slit, captured everyone’s attention so powerfully that it led to the creation of Google Images to manage the search traffic. Twenty years later, JLo revisited that unforgettable moment at the Versace Spring/Summer 2020 show, closing the runway in an updated version of the iconic piece. And just last year, Emily Ratajkowski brought it back as her Halloween costume. –Shinnie Park

Year: 2008

Kanye West has an abundance of memorable Grammys style moments to pick from. Remember his Tony Montana steeze from 2006? If we had to choose one that stands above the rest, it has to be this performance look from 2008. The custom LED jacket designed by Matthew M Williams and costume designer Erin Hirsh paired with glowing shutter shades perfectly embodied the Graduation era. But the lasting impact of this outfit is the footwear. This is when the world was first introduced to the Nike Air Yeezy. While the exact colorway that he wore that night was never released, the Air Yeezy would hit stores in three color schemes one year later. It is still hailed as one of the most important sneaker designs ever. In 2021, it even sold at a Sotheby’s auction for $1.8 million. Who would have thought that this was the night a generational sneaker empire would begin? –Mike DeStefano

Year: 2014

In 2014, Pharrell was at his commercial peak. Most of it had to do with his music. His single “Happy” from the Despicable Me soundtrack and a feature chorus on Daft Punk’s “Get Lucky” were unavoidable that year. There was also the abnormally-shaped vintage Buffalo Hat by Vivienne Westwood and Malcolm McLaren that he wore to the Grammys. Viral may be an understatement. This big ass headwear took over the public consciousness for months on end. It even had its own Twitter account (a simpler time). Fashion folks applauded the risky fashion choice while many in the general public laughed. Some said it looked like Smokey the Bear’s hat or the Arby’s logo. The fast food chain actually purchased the brown hat for $44,100 through a charity auction two months after Pharrell’s Grammys appearance. To this day, it’s easy to visualize Pharrell with this hat on his head, and he hasn’t worn it in over a decade. That’s icon status. –Mike DeStefano