When it comes to the Grammys, the Red Carpet arrivals can be even more entertaining than the awards. It’s the one night when all of the biggest names in music come together to honor the industry’s best. And whether their looks get people to turn their heads or turn up their noses, there are some stars that you can always count on to wear something that has everyone talking the next day. We’ve gone back in time to dig up some of the most unforgettable Grammy looks.
Jennifer Lopez – 2000
The pop diva turned heads when she arrived with then-boyfriend Diddy in this green Versace gown at the 2000 Grammy Awards. J. Lo’s jungle print dress took plunging neckline to a whole new level giving fans a peek at her navel. And Lopez showed everyone she’s still got it when she wore an updated version of the dress at the Versace spring 2020 show during Milan fashion week.
Nicki Minaj – 2012
Nicki Minaj made a serious red carpet statement when she appeared at the 2012 awards. Her red Versace cape with beaded accents and the blonde wig was an interesting choice. But it was the man on her arm, who was dressed in a pope costume, who had everyone talking.
Pharrell Williams – 2014
Pharrell Williams won the Grammy for Record of the Year in 2014 for Get Lucky. But if you don’t remember that, it’s probably because all you can remember is the hat he wore to the ceremony. The brown derby hat will definitely go down in Grammy fashion history. It even got its own Twitter handle @Pharrellhat that grew to more than 16,000 followers after the show.
Lil Nas X – 2020
The 2020 Grammys were huge for Lil Nas X. The Old Town Road artist won two awards for his breakout hit song. And he lit up the red carpet, giving us kinky cowboy vibes in a hot pink Versace cowboy suit and hat with gold studded accents.
Toni Braxton – 2001
Toni Braxton was definitely not wearing shapewear on the 2001 red carpet. She turned heads in a Richard Tyler dress that left little to the imagination. “I’ve always gone a little risque with all my other awards [show outfits]. I decided that before I got married and had babies, I’d wear this,” the singer said.
Grace Jones – 1983
Before there was Lady Gaga or Madonna, there was Grace Jones. The model, singer and actress has always been a trendsetter who is never afraid to push the envelope. And she was giving us a whole lewk at the 1983 awards.
Cee Lo Green – 2017
Cee Lo Green walked the Grammy red carpet in a head-scratching look in 2017. The Forget You singer wore a gold outfit complete with face mask and gloves that had social media buzzing. One Twitter user wrote, “@CeeLoGreen looking like a Batman villain. #GRAMMYS.”
Billy Porter – 2020
Billy Porter does not come to play on the red carpet, and Grammy night 2020 was no exception. He stood out in a turquoise jumpsuit, silver fringed boots and matching makeup. But it was the custom-made lamp shade-inspired hat with motorized closure that made him a standout.
Prince – 1988
Throughout his career, Prince has had too many memorable fashion moments to count. He’ll be remembered for his style as much as his music. But this double breasted polka dot suit from the 1988 Grammy awards was something special.
Kanye West – 2006
Ye has never been afraid to take fashion risks. Back when he was still known as Kanye West, the rapper channeled the 80s when he showed up to the 2006 awards in a lavender suit and white gloves.
Cardi B – 2019
Cardi B always slays on the red carpet. And in 2019, she did not disappoint. The rapper gave us oyster chic in a vintage Mugler Couture gown with pearl accessories and pink gloves.
Beyonce – 2017
Let’s face it, we could do a whole post on Beyonce’s award show looks alone. But the 2017 awards was something special. The gold Peter Dundas dress she wore helped the designer launch his line. But one of Queen Bey’s best accessories that night was the beautiful pregnancy glow she had while carrying twins Rumi and Sir.
Michael Jackson – 1984
Michael Jackson made history at the 1984 Grammys winning 8 awards, including Album of the Year. And the King of Pop sparkled on the red carpet in a sequined jacket, gold sash and his infamous glittery glove.
Rihanna – 2015
Rihanna always shuts the red carpet down with her show-stopping high fashion looks. The singer looked like a princess in a Giambattista Valli gown at the 2015 awards. The pink strapless tulle dress was perfectly complemented by neutral makeup and a simple updo.
Lil Kim – 2002
Lil Kim probably didn’t ride a motorcycle to the 2002 Grammys, but she definitely looked the part. The rapper wore a red leather suit with a white crop top that showed off some seriously toned abs. The Chanel bike helmet gave her even more biker chick street cred.
Alicia Keys – 2002
The 2002 awards show was full of unique looks and Alicia Keys was no exception. She glammed up her jeans with sheer turquoise dress and glittery eyeliner. Although the Girl on Fire singer’s style has definitely evolved over the years, this outfit is unforgettable.
Missy Elliot – 2002
Missy Elliot won two awards at the 2002 Grammy awards, taking home Best Pop Collaboration for Lady Marmalade and Best Rap Solo Performance for Get Ur Freak On. And she accepted her awards in a 70s-inspired purple suit with lots of detail.
Bootsy Collins – 2003
Legendary funk artist Bootsy Collins showed up to the 2003 red carpet in a white suit with zebra trim with a matching top hat and blinged-out shades. But knowing Bootsy’s history of making outrageous fashion choices, this may not even be his flashiest outfit.
Destiny’s Child – 2001
Bey’s mom Tina Knowles designed the glam green gowns the group wore to the 2001 Grammy awards. The girl group took home awards for their breakout hit Say My Name that night.
Jada Pinkett Smith – 1998
Jada Pinkett Smith was pregnant with son Jaden at the 1998 Grammy awards. And the actress had no problem showing off her baby bump in this glittery see-through maxi dress.
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