Scorecard Research Beacon
Search Icon
April 1, 2022

Grammys throwback: Remember these red carpet style moments from over 20 years ago?

WATCH: A look back at the best Grammys style moments from 1999

The 2022 Grammy Awards are Sunday night, and while we're excited to see the new crop of winners, we also can't help but reminisce about some of the most unforgettable red carpet moments from the past.

Throughout the years, we have seen everything from bucket hats to girl groups in matching looks be a the thing on the red carpet.

At the 41st Grammy Awards in 1999, musical artists like Jennifer Lopez, Celine Dion and Shania Twain showed up in everything from stick-straight hair to bright pastel eyeshadow to a sequin turtleneck dress. Perhaps, many of these trends might resurface for this year's affair.

Take a nostalgic scroll down memory lane and look at 10 amazing style moments from the Grammy Awards red carpet over twenty years ago -- 1999, to be exact.

MORE: Oscars style: Fashion blasts from the past
Editor's Picks

Purple Gaze

Celine Dion, Lauryn Hill, and more shined bright with purple eyeshadow on the red carpet.

PHOTO: Celine Dion attends the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.
Ron Wolfson/Getty Images
Celine Dion attends the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.
PHOTO: Lauryn Hill during the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.
SGranitz/WireImage/Getty Images
Lauryn Hill during the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.

Matchy-Matchy

Girl and guy groups like The Dixie Chicks and The Backstreet Boys as well as other dynamic duos like Brandy and Monica wore coordinating looks that demanded attention.

PHOTO: Brandy, left, and Monica attend the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.
KMazur/WireImage/Getty Images
Brandy, left, and Monica attend the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.
PHOTO: The Dixie Chicks attend the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.
Frank Trapper/Corbis via Getty Images
The Dixie Chicks attend the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.
PHOTO: The Backstreet Boys attend the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.
SGranitz/WireImage/Getty Images
The Backstreet Boys attend the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.

Stick-Straight Hair

Madonna and Jennifer Lopez sported stick-straight hair.

PHOTO: Madonna attends the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.
SGranitz/WireImage/Getty Images
Madonna attends the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.
PHOTO: Jennifer Lopez attends the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.
Kevin.Mazur/WireImage/Getty Images
Jennifer Lopez attends the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.

Head-to-Toe Silk

Silky ensembles and cut-outs commanded attention. Jada Pinkett wore it well.

PHOTO: Jada Pinkett Smith attends the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.
Ron Galella, Ltd./WireImage/Getty Images
Jada Pinkett Smith attends the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.

Crowning Glory

Raise your hand if you remember just how good Erykah Badu's headwraps were?!

PHOTO: Erykah Badu attends the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.
KMazur/WireImage/Getty Images
Erykah Badu attends the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.

Lady in Red

Whitney Houston turned heads in this red number with just the right glossy lipstick to match.

PHOTO: Clive Davis and Whitney Houston attend the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.
Steve.Granitz/WireImage/Getty Images
Clive Davis and Whitney Houston attend the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.

Sequined Turtleneck Dress

Shania Twain looks like a red carpet fashionista in her sequined turtleneck dress.

PHOTO: Shania Twain attends the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.
Vince Bucci/AFP/Getty Images
Shania Twain attends the 41st annual Grammy awards, Feb. 24, 1999, in Los Angeles.

Editor's Note: This story was originally posted on February 8, 2019.