What makes a celebrity award show outfit iconic? Is it the look’s shock value, its designer or the celebrity wearing it? When done right, it’s all of the above. Everything comes together for an ensemble that spans eras and gets immortalized forever. These 15 award show looks meet all the criteria. They have stopped the world in its tracks, made controversial statements and even helped to create web search engines.
From legendary and controversial rap artists to ghetto fabulous R&B singers and world-class actresses, award show fashion is a unique language that everyone likes to comment on. Let's get into 15 of the most iconic celebrity award show outfits of all time.
1. Michael Jackson at the 26th annual Grammy Awards
Michael Jackson made history at the 1984 Grammy Awards — in more ways than one. The King of Pop took home a whopping eight trophies, mostly for his critically acclaimed Thriller album. For the big night, he matched his wins with a regal red carpet outfit consisting of a custom-made navy and gold marching band jacket, black pants, aviator shades, shiny socks, black loafers and, of course, his legendary sequin white glove. It doesn’t get more iconic than that!
2. Jennifer Lopez at the 42nd annual Grammy Awards
Jennifer Lopez set the internet on fire at the 2000 Grammy Awards. She strut down the carpet wearing the famous green Versace dress with just enough fabric to keep her from indecent exposure. So many people were intrigued by her thigh-high split and low-plunging dress that Google created Google Images to help with the search. The famous look has become synonymous with the rise of internet pop culture. It has even been recreated many times over the years by J. Lo herself, comedians and as Halloween costumes.
3. Tupac at the 1996 MTV Video Music Awards
In what would be one of his final appearances, Tupac turned up at the 1996 MTV Video Music Awards in classic attire, but with a twist. He wore a grey suit over a lighter grey dress shirt and a complementing grey vest with detailed embroidery. He completed the unforgettable ensemble with lots of gold jewelry, including a chain, watch, bracelets and multiple rings.
4. Rihanna at the 2014 CFDA Fashion Awards
“Do my tits bother you?” was the iconic response that Rihanna jokingly gave one journalist while describing her outfit at the 2014 CFDA Fashion Awards. The beauty mogul delivered one of the most memorable looks of all time, wearing a Swarovski crystal-covered gown by Adam Selman with matching gloves and a headpiece. That same night, Rihanna also won the well-deserved Fashion Icon Award. She definitely shined bright like a diamond, landing herself right into the history books!
5. Lil' Kim at the 1999 MTV Video Music Awards
Lil’ Kim has flaunted many remarkable looks in her career; however, her show-stopping one-shouldered purple jumpsuit will always stand out. At the 1999 MTV VMAs, the rapper’s pasty was seen around the world. She completed the ensemble with purple hair, platform stilettos and matching pasties on her arm. Also, who could forget the iconic moment when Diana Ross tapped the New York artist’s exposed breast while presenting onstage with her and Mary J. Blige?
6. The Notorious B.I.G. at the 1995 Billboard Music Awards
The Notorious B.I.G. showed up at the 1995 Billboard Music Awards in style. He donned a textured black overcoat, cream turtleneck, black slacks and a Hip Hop style staple: The Clarks Wallabees. Biggie topped it all off with gold jewelry and a black top hat, proving that bigger guys have style too.
7. Aaliyah at the 2000 MTV Video Music Awards
The multitalented style icon was on full display in her Roberto Cavalli dress at the 2000 MTV Video Music Awards. The look was so ahead of its curve for its sexiness and sleek beauty, which was only compounded by Aaliyah’s natural allure that defined any outfit she wore. It has even been recreated several times in the past years.
8. Kanye West at the 2009 MTV Video Music Awards
Kanye West has had many notorious outfits over the years, but his 2009 MTV VMAs look changed both his image and pop culture forever. He kept it casually dressy for the red carpet, sporting a black leather shirt, Balmain jeans and black Timberland boots. Say what you want, but a Hennessy bottle has to be one of the most iconic accessories of all time.
9. Janet Jackson at the 1995 MTV Video Music Awards
Only Janet Jackson could make a fitted white crop top and black slacks look so chic! Such was the case at the 1995 MTV VMAs when she showed up with a big statement embroidered on the back of her simple outfit. Reportedly, she wore the cropped T-shirt in support of her brother, Michael Jackson, during his child abuse allegations. The award-winning songstress completed the timeless garb with her elegant figure and a red ribbon in support of the HIV/AIDS crisis.
10. Cardi B at the 61st annual Grammy Awards
Cardi B had a star-making night at the 2019 Grammy Awards, during which she took home the coveted award for Best Rap Album. The Bronx native wore three impressive looks by Thierry Mugler; however, the most famous was the instantly recognizable vintage Mugler Couture 1995/1996 red carpet gown. The dress featured a clamshell-like opening at the waist that solidified the "Bodak Yellow” rapper as a style icon to watch on red carpets for years to come.
11. Mary J. Blige at the 38th annual Grammy Awards
The undisputed Queen of Hip Hop & Soul put on a full regal and expensive display at the 1996 Grammy Awards. Blige arrived in a full leopard print ensemble that screamed “unbothered.” She accessorized with a matching headscarf as well as black sunglasses, gloves and heels.
12. Toni Braxton at the 43rd annual Grammy Awards
Who could forget Toni Braxton's revealing, long white gown at the 2001 Grammy Awards? Capping off an amazing comeback year, the R&B singer turned heads as she glided through the night. The dress featured long slits on both sides, which were held together by a delicate gold waistband. Braxton completed her memorable look with blonde hair, minimal jewelry and a gold Grammy Award!
13. Nas and Kelis at the 50th annual Grammy Awards
Nas and then-wife Kelis got the world talking with their matching statement outfits at the 2008 Grammy Awards. The pair donned casual looks supporting Nas’ Untitled album, which was originally titled N**ger. The lyricist wore a black T-shirt with the N-word, baggy jeans and black Air Force 1s with a red “Queens” New Era fitted cap. Kelis, on the other hand, sported an embroidered bomber jacket with the N-word, gold skinny jeans and stilettos. The conviction with which the duo displayed their ensembles had all the ingredients for an iconic look, still ruffling feathers till this day.
14. LL Cool J at the 1996 MTV Video Music Awards
LL Cool J appeared at the 1996 MTV VMAs in classic ’90s fashion. He donned a full leather look that consisted of a black Vanson jacket, pants, gloves, boots and a matching headband. All-leather outfits are as timeless as they come, offering a tough and edgy feel. The “Mama Said Knock You Out” rapper definitely knocked them out style-wise with this one!
15. Nicki Minaj at the 53rd annual Grammy Awards
Nicki Minaj was every bit of the cat’s meow at the 2011 Grammy Awards in her bold, all-leopard-print outfit. The Young Money Entertainement rapper was quite the chameleonic character early on in her career, and this outfit is the perfect marker of that era. Part of what makes the look so iconic is the way in which it immediately takes you back to a specific time in music history that is now long gone.