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See The Most Daring Grammy Awards Looks of All Time

Story Center by Story Center
January 31, 2026
Reading Time: 12 mins read
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Sabrina Carpenter

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Originally appeared on E! Online

Get ready to adore these pitch-perfect looks.

After all, when it comes to the Grammy Awards, celebs like Harry Styles, Sabrina Carpenter and Miley Cyrus know how to show out on the red carpet.

For the One Direction alum—whose first new album in four years is set for release in March—the biggest night in music has been the perfect place to show off his most eccentric looks.

For instance, Harry turned the 2023 red carpet into a rainbow paradise with his multi-colored Egonlab jumpsuit featuring a glittering diamond pattern. And when the “Aperture” singer took the stage, he emerged in a silver jumpsuit adorned with hundreds of shimmering fringes.

This year’s award show at the Crypto.com Arena in Los Angeles will be an evening to remember, and not just because Harry is returning to the ceremony as a presenter. With Sabrina nominated in six categories at the Feb. 1 show, including Record of the Year and Best Pop Vocal Album, she is sure to dazzle on the red carpet.

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In fact, the “Manchild” singer proved she’s always had good taste when she stepped out at the 2025 Grammys in a daring powder blue JW Anderson backless dress featuring a pear-cut diamond pendant cascading down her back and an ostrich feather trim along the hem and hips.

Among the most daring looks came from Chappell Roan, whose 2003 Jean Paul Gautier spring/summer couture collection gown was worthy of any art museum. In fact, the blue-and-yellow look was literally imprinted with Edgar Degas‘ portrait of ballerinas on the skirt.

Sabrina Carpenter

Axelle/Bauer-Griffin/FilmMagic

The “Pink Pony Club” singer—who is nominated for Record of the Year and Best Pop Solo Performance this year—completed her look with a feathered headpiece featured in the original runway show. Chappell’s stylist Genesis Webb felt it was essential to have her client in archival couture.

“Regardless of the designer, I wanted something with history; something that carried weight beyond aesthetics,” she told Vogue last February. “Gaultier had been on my mind for her for some time, so I reached out, and when this particular archival piece was presented, I had an immediate visceral reaction. It wasn’t just an option, it was the dress. While I had several looks prepared for the fitting, this was the only one that truly aligned with the vision.”

As the curtain slowly begins to rise on the 2026 Grammys, keep reading for more celebs who didn’t need any luck, babe, when it came to red carpet fashion.

Jennifer Lopez

Jennifer Lopez

Green with envy! J.Lo shut down the red carpet at the 2000 Grammys in a daring green Versace design. The fashion moment was so iconic that Google Image Search was born.

Rihanna

Rihanna

The Fenty Beauty founder looked like a vision in white at the 2011 Grammys. She turned heads in a sheer off-the-shoulder dress by Jean Paul Gaultier.

Cher

Cher

The legendary star basically invented daring fashion, and this white-hot number from the 1974 Grammys further cemented her status as a risk-taker.

Chappell Roan

<p>Chappell Roan</p>

The “Good Luck, Babe” singer channeled her hit song’s cover art with a pig-nose and red Renaissance-era inspired dress at Universal’s 2024 Grammy Awards after-party.

Lil Nas X

Lil Nas X

Lil Nas X made the red carpet his runway in a bright and bold pink Versace suit. From the daring harness to the gold-studded details, this was an outfit to remember.

Noah Cyrus

Noah Cyrus

The Best New Artist nominee made a sartorial splash at the 2021 Grammys in this larger-than-life couture design by Schiaparelli.

Doja Cat

Doja Cat

Dare to bare! The “Say So” rapper took the plunge in a very low-cut Roberto Cavalli gown at the 2021 Grammys.

Lady Gaga

Lady Gaga

Galactic glam vibes. The pop star is known for her over-the-top getups and she didn’t disappoint at the 2010 event when she showed up in a futuristic Armani Privé dress.

Cardi B

Cardi B

The “WAP” rapper made a tremendous splash at the 2019 ceremony with her vintage Thierry Mugler creation, which featured an oyster-like shell and dazzling pearl embellishments. Inspired by Sandro Botticelli‘s “The Birth of Venus,” this look was a work of art.

Harry Styles

<p>Harry Styles</p>

Jasmine Sanders

Jasmine Sanders

Florals for spring? Well, Jasmine Sanders certainly made it groundbreaking with her sheer lace gown by Jean Louis Sabaji.

Toni Braxton

Toni Braxton

The Grammy winner proved a dress can be regal and risquè all at the same time.

Paula Abdul

Paula Abdul

All that glitters is gold. Paula Abdul brought the glitz and the glamour to the 1990 ceremony with her dazzling gold fringe dress.

Spice

Spice

The Grammy nominee rivaled the red carpet in a larger-than-life ruffled robe that she paired over a plunging diamond-embellished dress.

Machine Gun Kelly

<p>Machine Gun Kelly</p>

In case his silver-foil Dolce & Gabbana suit wasn’t fabulous enough, MGK took his 2023 Grammys look to the next level with a glimmering crystal harness.

Billie Eilish

Billie Eilish

You should see her in a crown—or rather, a patterned suit complete with its own matching bucket hat and protective face mask as part of COVID-19 protocols.

Billy Porter

Billy Porter

The Pose star stole the show at the 2020 Grammys in a glitzy teal jumpsuit that was embellished with diamond fringe. However, the motorized hat really took things to the next level.

Jada Pinkett Smith

Jada Pinkett Smith

The Red Table Talk host’s nude-colored dress turned heads with its risquè cut-outs and body-hugging material. The knee-high strappy sandals added extra oomph.

Miley Cyrus

<p>Miley Cyrus</p>

The Disney alum dabbled with some heavy metals, stepping onto the 2024 red carpet in a custom Maison Margiela gold metal mesh dress. And, of course, she paired it with matching metal panties.

Sheryl Crow

Sheryl Crow

Sheryl Crow was nominated for “The First Cut Is the Deepest” at the 2005 Grammys—and she played it up by serving bawdy and face in a bright yellow gown with an exposed midriff and thigh-high slit.

TLC

TLC

The girl group proved sportswear could be just a chic and stylish as evening wear.

Tyler, the Creator

Tyler, the Creator

Inn-credible! The rapper donned an electrifying pink bellhop suit that he accessorized with a matching suitcase. And naturally, the clothes he would wear later that evening were tucked inside his luggage.

Beyoncé

Beyonc&eacute;

Queen Bey showed up and showed out wearing a majestic purple get-up. From the dazzling embellishments to the sheer material, the singer stunned from head-to-toe.

Lil’ Kim

Lil' Kim

The Grammy-winning rapper set the red carpet in flames with her vermilion-colored ensemble. The star’s Chanel motorcycle helmet and jewel-encrusted belt brought the wow factor.

For the latest breaking news updates, click here to download the E! News App

‘ The preceding article may include information circulated by third parties ’

‘ Some details of this article were extracted from the following source www.yahoo.com ’

Tags: chappell roanGrammy AwardsHarry StylesJean Paul Gautiermiley cyrusred carpetred carpet fashionSabrina Carpenter
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