By Neia Balao
4:57am PDT, Aug 27, 2020
In celebration of the MTV Video Music Awards on Aug. 30, 2020 — the first award show to take place in New York City amidst the coronavirus pandemic — Wonderwall.com is taking a look back at the best fashion moments from the VMAs 20 years ago! First up is late R&B singer Aaliyah. At the 2000 MTV VMAs, the 21-year-old "Rock the Boat" hitmaker, who took home awards for best female video and best video from a film, attended the event in this gorgeous animal-print dress by Roberto Cavalli. The frock has gone down as one of Aaliyah's most iconic looks, with stars like Kim Kardashian West rocking a version of it 20 years later. Keep reading for more nostalgia-inducing style moments…
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Does it get more '00s than this? At the 2000 MTV VMAs, Jennifer Lopez rocked a bedazzled cropped tank by then-boyfriend Diddy's fashion line, Sean John, with a pair of low-rise white pants. Jenny from the Block, who took home the Moonman for best dance video for "Waiting for Tonight" that year, completed the look with a white rhinestone-emblazoned bandana, a glitzy belt and jewels plus matching hoops.
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Leave it to Destiny's Child to stun on the red carpet! Beyonce, Kelly Rowland and Michelle Williams attended the 2000 MTV VMAs in custom coordinating leather ensembles by Bey and mom Tina's fashion line, House of Deréon. From the flattering corset tops to the delicate rhinestones, the trio, who took home the Moonman for best R&B video for "Say My Name" that year, made a sleek statement.
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At the 2000 MTV VMAs, Britney Spears sported one of her most iconic looks ever. During her medley performance of The Rolling Stones' "Satisfaction" and her own "Oops! I Did It Again," Britney tore off her sparkly pinstripe suit to reveal this rhinestone-studded two-piece ensemble by David Dalrymple. True to form, the young pop star — who was up for four awards that night including best pop video — put on an electrifying, midriff-baring performance!
Before taking the 2000 MTV VMAs stage to perform her iconic medley, Britney Spears kicked off the night in this plunging black gown. Complete with a dramatic thigh-high slit, the figure-flattering dress was a total hit.
Grammy Award-winning singer-songwriter Pink sported a bold look at the 2000 MTV VMAs. The "You Make Me Sick" hitmaker attended the event in furry floor length coat, a gold crop top, super-low-rise jeans and some very interesting gold heels. The spunky artist, who was nominated for best new artist, also rocked her then-signature hot pink hair.
Can you smell what The Rock is cooking?! While he's now recognized as Hollywood's highest paid actor (for the second year in a row), Dwayne Johnson was once a WWF superstar. The then-professional wrestler attended the 2000 MTV VMAs in this head-to-toe gold look. Ombre sunglasses, matching gold jewelry and a vest without a shirt?! Believe it or not, Dwayne was incredibly on-trend at the time.
The members of *NSYNC pulled out all the stops at the 2000 MTV VMAs. From Justin Timberlake's cream turtleneck (and entirely visible tank beneath it) to JC Chasez's shiny snakeskin pants to the rhinestone-emblazoned flames on Lance Bass' jean jacket, there was a lot happening here. That night, the boy band took home three awards: best pop video, best choreography and viewer's choice for "Bye Bye Bye."
"Candy" and "I Wanna Be with You" pop star Mandy Moore attended the 2000 MTV VMAs in this simple, neutral ensemble. The fresh-faced singer was just 16 at the time!
In promotion of his eighth studio album, which was released five days after the 2000 MTV VMAs took place, LL Cool J attended the award show in a custom jean jacket and hat that read "The G.O.A.T." It went on to become LL's first and only album to hit No. 1 on the Billboard 200 chart.
Pop star Christina Aguilera arrived at the 2000 MTV Video Music Awards wearing a stomach-baring black dress covered in gold embellishments. Next, see what she wore on stage…
Britney Spears wasn't the only pop star who performed a medley at the 2000 MTV VMAs. For a performance of her chart-topping hits "Genie in a Bottle" and "Come On Over," Christina Aguilera traded the sexy black dress she'd worn on the red carpet for a bedazzled red two-piece leather look on stage. In typical '00s fashion, the "What A Girl Wants" singer, who earned five nominations including best new artist and best pop video, sported a triangle-cut crop top.
Looks like Dwayne Johnson wasn't the only one to go shirtless at the 2000 MTV VMAs! That night, Sisqó, who took home the Moonman for best hip-hop video for "Thong Song," rocked a coordinating patchwork leather ensemble. He finished the denim-inspired look with his signature dragon pendant.
Not long after she starred in "10 Things I Hate About You," Julia Stiles stepped on the red carpet at the 2000 MTV VMAs. The then-19-year-old actress looked precious in this pink satin spaghetti-strap dress. She completed the simple look with a very tiny, very '00s purse.
Tara Reid posed for photos on the 2000 MTV VMAs red carpet in a getup that was definitely true to the time! The "American Pie" star, who attended with her then-boyfriend — MTV host Carson Daly — wore a gray halter top and low-rise tie-dye gray pants. Her leopard-print cuffs, icy eyeshadow and frosted lip were the finishing touches to her '00s cool-girl look.
We love a coordinating moment! At the 2000 MTV VMAs, Eve — who was up for best rap video for "Love Is Blind" — hit the red carpet in absolute style. She wore a gold off-the-shoulder minidress with a chunky statement choker. To complete the look, the "Let Me Blow Ya Mind" rapper rocked a red lip, red shawl, knee-high red boots and, of course, fiery red hair!
Kate Hudson, who was just 21 at the time, attended the 2000 MTV VMAs wearing a plunging white pantsuit with a sparkly pink top. The following year, she won a Golden Globe and earned a best supporting actress nomination at the Academy Awards for her breakout role in "Almost Famous," which debuted six days after VMAs.
At the 2000 MTV VMAs, Macy Gray rocked a '70s-inspired look. From the tie-dye bell bottoms to the fringe vest, the "I Try" hitmaker, who took home the awards for best cinematography and best new artist that night, looked ready to dance the night away!
Two years before his iconic track "Hot In Herre" was released, Nelly hit attended the 2000 MTV VMAs. The rapper went with a casual-cool look, sporting a black tank, black hat and black Gucci logo-print pants. He completed the look with his signature "Nelly" pendant!
Unfortunately, not all looks were showstoppers. At the 2000 MTV VMAs, actress-model Milla Jovovich wore a peculiar-looking tank top with matching black pants. She added pops of color with her pointy pumps, a chunky pearl necklace and a camel-colored purse.
Another model who attended the 2000 MTV Video Music Awards? Brazilian beauty Gisele Bündchen, who made her VMAs debut that year! The then-Victoria's Secret model hit the red carpet in a white turtleneck gown and brown knee-high boots. Twenty years later, Gisele's still pulling out looks we wouldn't dare try.
Grammy-winning rapper Wyclef Jean arrived at the 2000 MTV VMAs in a white waistcoat and matching pants. The "911" hitmaker went for neutral tones with his camel-colored turtleneck, brown loafers and taupe brimmed hat.
Fresh-faced supermodel Heidi Klum wore a one-shoulder minidress to the 2000 MTV VMAs. She paired the glitzy gown covered in beaded detailing with strappy black sandals and a matching shoulder bag.
Two years before landing his acclaimed role in "Brown Sugar," Taye Diggs attended the 2000 MTV VMAs. The actor, who at the time had previously appeared in films like "How Stella Got Her Groove Back" and "House on Haunted Hill," sported a dark gray long sleeved top and black leather pants.
Dwayne Johnson wasn't the only WWF superstar to attend the 2000 MTV VMAs. Late professional wrestler Joanie Laurer — better known as Chyna — hit the red carpet in this superhero-inspired ensemble. From the very Wonder Woman-esque corset top to the matching red leather pants and headband, it was nothing short of a bold look!
Rounding off our list is supermodel Alek Wek, who opted for a chic, monochromatic look at the 2000 MTV VMAs. The trailblazing beauty, who's credited with revolutionizing the fashion industry's perception of beauty, looked catwalk-ready in this coordinating orange ensemble and matching square-toe kitten heels. She finished the look off with an adorable multicolored shoulder bag.
