The annual MTV Video Music Awards are this Sunday. While the show doesn’t hold the same weight as it did throughout the 2000s, it does have plenty of iconic moments that are worth looking back on. Many of them are tied to the ensembles that some of music biggest stars decided to pull up to the event wearing or hit the stage in.
This list isn’t strictly examining who the best dressed stars in VMAs history have been. Instead, we are spotlighting the 10 looks that are still being referenced and talked about to this day, from Slim Shady and his army of Stans in white T-shirts to Lady Gaga covered in a couture look made of raw meat.
Ahead of Sunday night’s show, take a trip down memory lane and look back at the 10 most memorable MTV VMAs looks of all time.
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Tyler, The Creator (2011)
Year: 2011
Throughout his career, Tyler, The Creator has turned award shows into occasions to debut intricate, thematic looks that tie back to his current album era. Back in 2011, he was still just a rookie who loved Supreme and loitering on Fairfax Avenue. The rebellious and outspoken leader of Odd Future accepted his “Best New Artist” award dressed in an outfit that has been replicated thousands of times over by his loyal fanbase since. That olive green Supreme cap with a leopard brim is still valued to this day because of this moment.
Busta Rhymes (1997)
Year: 1997
Busta Rhymes has solidified his place as one of the best dressed New York rappers of all time. His boundary-pushing stylistic choices in the ‘90s like this one are a big reason why. Busta pulled up to the ‘97 VMAs in a custom red and gold Indian kurta. To add to the unorthodox moment, Busta went on to present an award beside Martha Stewart later that night.
Eminem (2000)
Year: 2000
Not every memorable style moment needs to be attached to a major fashion house or feature avant garde clothing. Case in point, Eminem at the 2000 VMAs. The outfit itself was nothing special: a white tee, grey sweatpans, and a white baseball cap. What made it memorable was the spectacle of 100 lookalikes, complete with bleached blonde hair, following Em as he made his way into Radio City Music Hall performing "The Real Slim Shady" and "The Way I Am." It showed the influence of Em at the peak of his popularity. Over 20 years later, this one lives on of the best visuals that the VMAs have ever produced.
Rihanna (2016)
Year: 2016
No stranger to a memorable style moment, of course Rihanna had to end up on this list. For her show-opening performance in 2016, she wore this incredible pink Hood By Air look that paired a simple ringer T-shirt with a leather corset and chaps. It’s not just one of the most memorable looks in VMAs history, but one of the most memorable of her career. Considering how many of those Rihanna has had, that’s saying something.
Outkast (2001)
Year: 2001
Andre 3000 and Big Boi never shied away from making a statement. It’s that type of energy that made them two of the best dressed Atlanta rappers of all time. Part of what made Outkast’s style so great is that, even though both members had different tastes, they always found a way to make their looks harmonious. Take this moment from the 2001 VMAs. Big Boi opted for baggy pink fur shorts, a white graphic tee, pink beret, and classic “Linen” Air Force 1s. Three Stacks went with a green fedora, pink/green overalls, and snakeskin leather boots. Both are maximalist in their own way, but make sense together because of their vibrant color palettes. To this day, no rap group has ever done style quite like Outkast.
Lady Gaga (2010)
Year: 2010
Lady Gaga loves pulls out all of the stops for her red carpet looks. Nothing has ever been able to come close to the infamous meat dress. This is no illusion. Designer Franc Fernandez made a dress for the pop star out of flank steak. What more can really be said here?
Pharrell and NIGO (2006)
Year: 2006
For the most part, Pharrell and NIGO have left this level of audacious dressing behind them, but it will live on forever as a symbol of 2000s streetwear. The duo behind BBC ICECREAM showed up the to the ‘06 VMAs decked out in full BBC and Bape fits. The legendary Jacob and Co. diamond chains hanging from their neck were just the cherry on top. Who needs a lookbook when you can pull up looking this cool in your own brand?
Britney Spears (2001)
Year: 2001
At the height of her superstardom, Britney Spears hit the stage at the ‘01 VMAs to perform “I’m a Slave 4 U,” and delivered one of its most iconic performances of her career. The green top, embellished shorts, and gladiator sandals were important parts of the look. But what makes this one so memorable is the 7-foot long, 20-pound albino Burmese python that was rested on her shoulders midway through the performance. The visual lives on as one of the defining moments of VMAs history.
Kanye West (2010)
Year: 2010
Kanye West may have more infamous VMAs moments, but when it comes to style, nothing come close to his return to the VMAs stage in 2010 to debut “Runaway.” Before the “Red October” Air Yeezy 2s, Mr. West was already owning the bright red look. He turned heads in a monochromatic suit paired with matching Louis Vuitton Dons. The striking look made for the perfect comeback moment. It has become one of the defining outfits of West’s historic career. Shoutout to Pusha T for popping out in the salmon-colored suit to spit his verse too.
Lil’ Kim (1999)
Year: 1999
When Lil’ Kim arrived at the ‘99 VMAs, her look already had everyone talking. Her purple jumpsuit made of Indian bridal fabric and seashell pastie was responsible for even more shock value later on that night when co-presenter Diana Ross couldn’t resist jiggling Kim’s exposed breast on stage.
“I wanted to make something really ornate and feminine and pretty, to offset the fact that she had one breast out," Kim’s stylist Misa Hylton told Pop Sugar in 2020. “The glamorous, sexy outfit was complemented by a monochromatic lilac wig by Diane Alexander and silver glitter platform mules by Steve Madden.”
In an era before social media virality, this look and moment took the pop culture news cycle by storm. This type of look is part of what made Lil’ Kim one of the most influential and impactful style icons in rap history. To this day, there hasn’t been a VMAs look quite like it.
