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Sisqo
Image Credit: Ron Galella, Ltd./Ron Galella Collection via Getty Images In the thick of “Thong Song” success, Sisqo made an equally big statement at the 42nd Annual Grammy Awards. Decked in bright orange leather pants, and a matching hooded vest, it was hard not to spot him.
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Eve
Image Credit: Ron Galella, Ltd./Ron Galella Collection via Getty Images Eve brought the boss energy to the 27th Annual American Music Awards. She completed her bedazzled purple pants and pink tank top with a matching floor-length fur coat and a floppy hat. Keeping the monochromatic look in check, she added some purple eyeshadow and a berry lip.
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Destiny’s Child
Matching was certainly the theme of the year 2000. We love this Destiny’s Child sparkling look, in which each member wears a variation of the same outfit to compliment their personal style.
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Aaliyah
Image Credit: Ron Galella, Ltd./Ron Galella Collection via Getty Images The low-rise leather pants scream 2000. Aaliyah made the look more rock-chic with a cropped black and jeweled tank top and cool-girl shades.
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Fred Durst
Image Credit: Steve Granitz/WireImage Fred Durst owned the go-to casual look for guys in the 2000 era, which included a baggy t-shirt with baggy pants, sneakers and (of course) a hat worn backwards.
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LeAnn Rimes & Violet Sanford
Image Credit: Getty Images If you’re dancing on the bar, you gotta look cute. In “Coyote Ugly,” LeAnn Rimes and Violet Sanford’s outfits included a lot of crop tops, low-rise pants and big Western-themed belts.
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Mariah Carey
Image Credit: Evan Agostini/Getty Images Mariah Carey paid tribute to her 1997 album ‘Butterfly’ three years later when she walked the red carpet for “VH-1 Divas 2000: A Tribute To Diana Ross.” She paired her iconic, sparkly butterfly-shaped crop top with a waistband-less pair of blue jeans and heels.
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Jennifer Lopez
Image Credit: Scott Gries/ImageDirect Jennifer Lopez in Versace at the 42nd Grammy Awards held in Los Angeles on February 23, 2000.
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Britney Spears
Image Credit: Scott Gries/Getty Images Britney Spears was the queen of crop tops back in 2000, and stunned in this onstage look at the 2000 MTV Video Music Awards. Her nude-colored bra and pants combo provided for an illusion that her actual skin was covered in jewels.
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NSYNC
Image Credit: Nick Elgar/ImageDirect *NSYNC rolled up to the MTV Video Music Awards looking very 2000. From the fur coats to the colored sunglasses and Justin Timberlake’s ramen noodle curls, the boy band’s look was on-point for the era.
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Christina Aguilera
Image Credit: Frank Micelotta/ImageDirect Christina Aguilera also showed off her midriff performing at the 2000 MTV Video Music Awards. Like Britney, she also opted for a matching crop top and pants combo, but Xtina’s look was a bit more fiery in a bright red hue with sparkling accents.
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Pink
Image Credit: Ron Galella, Ltd./Ron Galella Collection via Getty Images) P!nk put on her own spin on the popular crop top at the Second Annual Teen Choice Awards. She matched her fittingly pink hair, with a see-through collared crop top, hoops and low rise jeans.