By Megan Riedlinger
11:06am PDT, Aug 22, 2019
Today we're gonna party like it's 1999! To celebrate the 2019 MTV Video Music Awards, which air on Aug. 26, Wonderwall.com is takin' it all the way back to the '99 VMAs red carpet where sparkles, crop tops and leather reigned supreme. First up? TLC, who decided to match on the big night. They were the proud winners of best group video for "No Scrubs," and rocked complementary black two-piece ensembles in a shimmering fabric, all with their own twists. T-Boz's look had sleeves, Lisa "Left Eye" Lopes went with a halter-style bralette and skirt, and Chilli's ensemble featured a choker and strapless bandeau top paired with pants.
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Her debut song "If You Had My Love" might have lost out in every category in which it was nominated at the MTV VMAs that year, but there was no denying that Jennifer Lopez arrived in style. The actress-turned-singer sported this fringed halter tank paired with a metallic skirt with a thigh-high slit. Completing her look? Knee-high stiletto boots.
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The most iconic ensemble that year? Lil' Kim's! Her crazy purple jumpsuit went down in infamy thanks to one feature — or lack thereof: It was missing a full sleeve and half of its bodice! The rapper instead sported a sparkling pasty to prevent a massive wardrobe malfunction, making this look legendary in the process. Keep reading for more MTV VMAs fashion from two decades ago…
RELATED: Our favorite moments from MTV VMAs past
A look that would fly today? Lauryn Hill's sleek red leather dress! From its buttons and length to the way she paired it with tan knee-high boots, this look was a winner just like Lauryn that night: She took home four Moonmen including for video of the year and best female video for "Doo Wop (That Thing)."
Back in the '90s, boy bands had a tendency to match. It looks like *NSYNC loosely tried to unify their wild looks at the 1999 MTV VMAs — each rocked some sort of green hue — but aside from that thread, their looks were all over the place! From Justin Timberlake's leather and JC Chasez's suede to Lance Bass's out-of-place suit, Chris Kirkpatrick's shiny pleather and Joey Fatone's wild shiny trench coat, the band provided a stellar example of all the worst elements of late-'90s fashion.
The other big boy band of the era, Backstreet Boys, opted for a unified thread — shades of brown — within their 1999 MTV VMA getups. Nick Carter rocked a suede jacket, Howie Dorough went with sparkles, Kevin Richardson wore gray with bronze embellishments, AJ McLean opted for a cream tank top and snakeskin trousers and Brian Littrell rocked a brown leather jacket and dress shirt combo.
Britney Spears walked the red carpet in this very '90s garb — a belly-baring metallic bronze jacket paired with super-sparkly low-waisted pants. She performed her then-debut single "…Baby One More Time," in a joint performance with *NSYNC.
Britney Spears' second look of the night? This sparkly and slinky black number that showed plenty of skin thanks to a sheer top trimmed with a ton of feathers.
Hot pink and leopard print was a trendy combo in the '90s, as Christina Aguilera proved at the 1999 MTV VMAs. Her sheer tank was trimmed with hot pink lace. She tucked it into a black miniskirt and topped the look with more leopard in the form of her silky jacket. Finishing things off? Those nearly knee-high flat black boots. The star didn't have any nominations that night though still came to present best rock video with Tommy Lee.
JAY-Z rocked Rocawear at the MTV VMAs in 1999 with the addition of a sparkly chain with a cross. He won best rap video for "Can I Get A…" that night and also performed a medley of his hits.
Pamela Anderson certainly opted for a statement look at the 1999 MTV Video Music Awards. The star's bizarre getup included a white corset with sparkly, embellished pants paired with an equally embellished belt all topped with a pale pink feathered hat because… why not!
A trenchcoat, a striped hat and Converse high tops? Yep, that's what Tommy Lee — who attended with ex-wife Pamela Anderson during a brief reconciliation — wore to the 1999 MTV VMAs, where he presented best rock video with Christina Aguilera.
Decades before she joined "The Real Housewives of Beverly Hills," Denise Richards donned these sparkly coordinates at the 1999 MTV VMAs. She paired her getup with a disastrous trend of the times — heeled flip-flops!
Best male video winner (for "Miami") Will Smith dressed to impress at the 1999 show! The star rocked a black-and-white hide jacket over top an all-black ensemble.
They matched! Jada Pinkett Smith opted for this black-and-white leather ensemble at the 1999 award show. She was on hand as nominee hubby Will Smith's date.
We could see this frock on a red carpet in 2019! Rebecca Romijn — who went by Rebecca Romijn-Stamos back then — donned this sweet printed column dress with spaghetti straps at the MTV VMAs in 1999.
The men of Korn won best rock video and best editing in a video for "Freak on a Leash. They attended clad in a lot of leather and denim (and one stark white top hat!).
Recognize this actress? Back in 1999, Heather Donahue was best known for starring in the indie horror hit "The Blair Witch Project." She arrived at the MTV VMAs in this crop top and sequined pants combo.
One of the strangest looks on the red carpet in 1999 belonged to Moby, who was on hand to DJ during the award show's commercial breaks! The musician rocked this super-shiny gold suit with a bronze and equally shiny dress shirt underneath — tying it all together with more gold in the form of a bow tie.
Charlotte Church was feeling blue at the 1999 MTV VMAs! The young Welsh singer, who was on hand to present best new artist, sported head-to-toe shades of blue — a three-quarter-length boat-neck top and a shiny blue floor-length skirt.
Crop tops were all over the 1999 MTV VMAs red carpet, and Heather Locklear embraced the trend. She wore this black one with a pair of shiny low-slung trousers when she presented best pop video.
Check out Lenny Kravitz's psychedelic suit! He topped it with an even more unorthodox accessory — a feathered boa — at the 1999 MTV VMAs.
Mira Sorvino presented best male video at the 1999 MTV VMAs in this pretty silver column-style gown. The dress's spaghetti straps and shimmering fabric would fit in on a red carpet today as well.
Heidi Klum opted for a sweet strapless floral frock at the MTV VMAs in 1999. The model wore the white knee-length dress with a pink-and-yellow floral motif to present the viewer's choice prize that night.
Sugar Ray's Mark McGrath rocked a shiny black leather getup at the MTV VMAs in 1999. His band's song "Every Morning" was up for best group video that year but lost out to TLC's "No Scrubs."
Kid Rock donned his signature questionable style at the MTV VMAs in 1999 — a baggy white button-down, track pants, Adidas sneakers and a red fedora. He left without winning a Moonman… or a best dressed nod!
