Will We See These Y2K Outfits From The 1999 Grammys Red Carpet Again?

We’re calling out the decade’s freshest stars.

Backstreet Boys
Photo: Ron Galella Getty Images

Jennifer Lopez

Steve Granitz Getty Images
1 of 21

In a gold shimmery minidress paired with strappy heels.

Celine Dion

2 of 21

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

Shania Twain

Ron Galella Getty Images
3 of 21

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

Missy Elliott

4 of 21

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

The Dixie Chicks

Frank Trapper Getty Images
5 of 21

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

Will Smith & Jada Pinkett Smith

Jeff Kravitz Getty Images
6 of 21

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

Related article: Will Smith And Jada Pinkett Smith Make First Red Carpet Appearance Since Oscars

Celine Dion

ABC/Getty Images
7 of 21

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

Usher

Ron Galella Getty Images
8 of 21

In a blue monochrome suit accessorized with lightly tinted sunglasses.

Backstreet Boys

Ron Galella Getty Images
9 of 21

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

Mary J. Blige

Steve Granitz Getty Images
10 of 21

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

Aaron Carter

Ron Galella Getty Images
11 of 21

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

Shanice

Ron Galella Getty Images
12 of 21

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

Steven Tyler

Frank Trapper Getty Images
13 of 21

In an oversized white suit and a black satin vest.

Lauryn Hill

Steve Granitz Getty Images
14 of 21

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

Diddy

Steve Granitz Getty Images
15 of 21

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

Natalie Imbruglia

16 of 21

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

Beck

Jeff Kravitz Getty Images
17 of 21

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

Chris Tucker

Ron Galella Getty Images
18 of 21

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

Madonna

Steve Granitz Getty Images
19 of 21

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

Related article: Madonna's Biopic About Her Own Life Gets Scrapped

Faith Hill

Ron Galella Getty Images
20 of 21

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

Jennifer Love Hewitt

Ron Galella Getty Images
21 of 21

In a calf-length strapless gray midi dress with simple black platform heels.

This article originally appeared in Harper's BAZAAR US.


Share this article