21 Outfits from the 1999 Grammys Red Carpet That Are So Retro It Hurts

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Jennifer Lopez

In a gold shimmery minidress paired with strappy heels.

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Celine Dion

In a white asymmetrical two-piece set paired with strappy clear sandals.

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Shania Twain

In a white sequined, long-sleeved turtleneck gown by Marc Bouwer.

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Missy Elliott

In a white co-ord, matching hat, brown top, and feather trim all over.

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The Dixie Chicks

In coordinating black sets, strappy heels, and silver safety-pin chains to accessorize, as styled by Todd Oldham.

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Will Smith & Jada Pinkett Smith

Will in a silver two-tone pleather suit; Jada in a two-piece champagne set with a matching headscarf; both accessorized with tinted spectacles.

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Celine Dion

In a sleek strapless gray gown featuring a shimmery netted shoulder strap.

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Usher

In a blue monochrome suit accessorized with lightly tinted sunglasses.

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Backstreet Boys

In a collection of black, red, and white suits accessorized with hats, jewelry, glasses, and rhinestone detailing.

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Mary J. Blige

In a white long-sleeved sweater with a furry vest on top paired with a matching hat, metallic jeans, and white heeled boots.

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Aaron Carter

In a bright mustard-yellow satin suit complete with a custom nameplate chain.

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Shanice

In a lavender velvet dress with a matching bolero and clutch.

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Steven Tyler

In an oversized white suit and a black satin vest.

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Lauryn Hill

In a semi-cropped black top and colorful statement maxi skirt coordinated with equally vibrant shimmery purple eye shadow.

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Diddy

In an all-navy suit, silk handkerchief and tie, and matching spectacles.

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Natalie Imbruglia

In a white trench coat embellished with mirror polka dots paired with a black blouse, dark jeans, chunky black boots, and a mini handbag.

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Beck

In a vibrant animal-print button-down paired with blue leather pants.

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Chris Tucker

In a red-and-black pullover, gym shorts, black sneakers, sunglasses, and a metallic red cap.

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Madonna

In blinged-out lavender pants paired with a white tank, bright pink eye shadow, and chunky beaded bracelets.

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Faith Hill

In a satin mid-length patterned dress with strappy heels topped with a headband.

Amanda Le is a contributing writer at Hearst Magazines, where she covers fashion, beauty, lifestyle, and entertainment. In her free time, you can find her thrifting her next outfit, traveling to new cities, crushing a boxing class, or eating her way through NYC!

Sabrina Park is a Digital Fellow at HarpersBAZAAR.com where she covers news, fashion, and culture stories. When she’s not writing she loves hanging out with her cat, reading outdoors and scrolling the depths of TikTok.

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