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Grammys 2024: Best, worst and weirdest red carpet looks of all time, from Taylor Swift to Jennifer Lopez

From Britney Spears to Olivia Rodrigo, take a look back at our favourite Grammys fashion hits and misses.

Take a look back at the best and worst Grammys red carpet looks of all time. (Getty Images)
Take a look back at the best and worst Grammys red carpet looks of all time. (Getty Images)

The 2024 Grammys are right around the corner, and music's biggest stars are preparing for what's bound to be a night full of fun fashion.

Unlike the Oscars or the Emmys, the Grammy Awards are a chance for celebrities to let down their hair and step outside the box when it comes to their red carpet style. There are no rules when it comes to the Grammys red carpet, but there are guaranteed to be a few looks every year that leave us scratching our heads.

When are the Grammys?

The 66th Grammy Awards will air live from the Crypto.com Arena in Los Angeles on Sunday, Feb. 4, 2024 at 8 p.m. ET/5 p.m. PT, with Trevor Noah back in the hosting seat for his fourth consecutive year.

Prior to the ceremony, "Live From E!: Countdown to the Grammys" will begin at 4 p.m. ET. The Associated Press will also stream its three-hour red carpet coverage on YouTube, X (formerly known as Twitter) and APNews.com starting at 5 p.m. ET. There will also be red carpet coverage on an improved digital experience at live.GRAMMY.com.

This year's show is dotted with performances from stars of several genres, including Billie Eilish, Luke Combs, Olivia Rodrigo, U2, SZA and Travis Scott. Canadian artist Joni Mitchell will also take the Grammys stage for the first time.

But ahead of the show this year, we're looking back at some of the biggest fashion hits and misses from the Grammy Awards' red carpet.

What did Yahoo readers say last year?

For last year's 65th Grammy Awards, Yahoo Canada readers were pretty dead set on their picks for best and worst dressed.

Out of more than 32,000 votes, 49 per cent of people said Taylor Swift was the best-dressed celebrity at the event when put up against Adele, Megan Fox, Lizzo and Cardi B.

BEST: Taylor Swift (2023)

Taylor Swift's navy blue two-piece gown for the 2023 Grammy Awards was created by Roberto Cavalli. (Photo by Allen J. Schaben / Los Angeles Times via Getty Images)
(Photo by Allen J. Schaben / Los Angeles Times via Getty Images)

The 12-time Grammy Award winner — who became the first female artist to win Album of the Year three times in 2021 — reflected the moody essence of her tenth studio album, "Midnights," at last year's red carpet. Her sparkling navy blue two-piece gown was created by Roberto Cavalli.

On the other hand, readers were also adamant about Harry Styles being the worst-dressed star on last year's red carpet, despite Kacey Musgraves, Shania Twain, Blac Chyna and Camila Cabello also missing the mark. Out of more than 26,000 votes, 44 per cent of people gave Styles that title.

WORST: Harry Styles (2023)

Harry Styles wore a multi-coloured EGONlab jumpsuit on the 2023 Grammys red carpet. (Photo by Jeff Kravitz/FilmMagic)
(Photo by Jeff Kravitz/FilmMagic)

On top of facing heat for his out-of-touch comment after winning Album of the Year for "Harry's House" at the 2023 Grammys, the "As It Was" singer looked a bit clownish wearing a glittering EGONlab patchwork jumpsuit and white boots.

But what other celebrities looked stunning on the Grammys red carpet over the years, and who faltered a bit in their style? Scroll through to see if your favourite celebrity's Grammys ensemble made our best or worst list.

BEST: SZA (2018)

NEW YORK, NY - JANUARY 28:  Recording artist SZA attends the 60th Annual GRAMMY Awards at Madison Square Garden on January 28, 2018 in New York City.  (Photo by Jamie McCarthy/Getty Images)
(Photo by Jamie McCarthy/Getty Images)

Despite receiving five nominations during the 2018 Grammys yet walking away empty handed, SZA looked ethereal in a silver gown with ornate beading and tulle designed by Atelier Versace. But the "Kill Bill" artist is sure to be a main star on this year's red carpet as she leads nominations with nine nods.

WORST: Kelly Osbourne (2011)

(Photo by Kevin Mazur/WireImage)
(Photo by Kevin Mazur/WireImage)

Kelly Osbourne might've looked pretty at the 2011 Grammys, but the purple asymmetrical mini dress from Tadashi Shoji she wore resembled a loofah well-past its expiry.

BEST: Olivia Rodrigo (2022)

LAS VEGAS, NEVADA - APRIL 03: Olivia Rodrigo attends the 64th Annual GRAMMY Awards at MGM Grand Garden Arena on April 03, 2022 in Las Vegas, Nevada. (Photo by Kevin Mazur/Getty Images for The Recording Academy)
(Photo by Kevin Mazur/Getty Images for The Recording Academy)

Olivia Rodrigo took home her first-ever Grammy Award for Best New Artist at the 2022 ceremony, and rocked a Vivienne Westwood gown with an optical illusion to walk the red carpet.

WORST: CeeLo Green (2017)

LOS ANGELES, CA - FEBRUARY 12:  Gnarly Davidson, CeeLo Green arrives at the 59th GRAMMY Awards on February 12, 2017 in Los Angeles, California.  (Photo by Steve Granitz/WireImage)
(Photo by Steve Granitz/WireImage)

We're not quite sure what was happening on the 2017 Grammy's red carpet, but CeeLo Green's Marvel villain reject look was one we can't forget — no matter how hard we try.

BEST: Dua Lipa (2021)

LOS ANGELES - MARCH 14: Dua Lipa  at THE 63rd ANNUAL GRAMMY® AWARDS, broadcast live from the STAPLES Center in Los Angeles, Sunday, March 14, 2021 (8:00-11:30 PM, live ET/5:00-8:30 PM, live PT) on the CBS Television Network and Paramount+. (Photo by Francis Specker/CBS via Getty Images)
(Photo by Francis Specker/CBS via Getty Images)

Dua Lipa radiated glamour in a Cher-inspired look by Versace that featured a bejewelled butterfly bodice and thigh-high slit for the 2021 Grammy Awards.

WORST: Pink (2002)

Pink (Photo by SGranitz/WireImage) *** Local Caption ***
(Photo by SGranitz/WireImage)

Pink hit the 2002 ceremony's red carpet in a gender-bending look that included asymmetric pants and a sequinned bra, along with a hot pink garter and a bow tie.

BEST: Beyoncé (2014)

(Photo by Jason LaVeris/FilmMagic)
(Photo by Jason LaVeris/FilmMagic)

Let's be honest, we could make an entire gallery of the best Beyoncé Grammy red carpet looks. But after changing into this white sheer lace Michael Costello gown following a performance of "Drunk in Love" with husband Jay-Z, it's clear why Queen Bey is, well, the queen.

WORST: Justin Bieber (2022)

LAS VEGAS, NEVADA - APRIL 03: Justin Bieber attends the 64th Annual GRAMMY Awards at MGM Grand Garden Arena on April 03, 2022 in Las Vegas, Nevada. (Photo by Jeff Kravitz/FilmMagic)
(Photo by Jeff Kravitz/FilmMagic)

Justin Bieber's oversized Balenciaga suit and platform monster Crocs definitely made a statement on the red carpet, but left fans confused by the look.

BEST: Mariah Carey (1991)

NEW YORK, NY - CIRCA 1991: Mariah Carey attends the 33rd Annual Grammy Awards circa 1991 in New York City. (Photo by Robin Platzer/IMAGES/Getty Images)
(Photo by Robin Platzer/IMAGES/Getty Images)

Mariah Carey arrived at her first-ever Grammy Awards in 1991 wearing a simple, elegant, rhinestone-edged, black, mini dress. She went home with two awards for Best New Artist and Best Female Pop Vocal Performance.

WORST: Blac Chyna (2023)

(Photo by Axelle/Bauer-Griffin/FilmMagic)
(Photo by Axelle/Bauer-Griffin/FilmMagic)

Blac Chyna explained her all-black feather body suit look for the 2023 Grammys resembled part of "her story, the phoenix." But the rhinestone outfit looked a bit more like something you'd see in the corner of your room at night when when you wake up with sleep paralysis.

BEST: Britney Spears (2000)

Britney Spears (Photo by Kevin Mazur/WireImage)
Britney Spears (Photo by Kevin Mazur/WireImage)

Britney Spears channelled Old Hollywood glamour with this stunning winter white look at the 2000 Grammy Awards, where she was up for Best New Artist and Female Pop Vocal Performance.

WORST: Pharrell (2014)

(Photo by Lester Cohen/WireImage)
(Photo by Lester Cohen/WireImage)

What was Pharrell hiding underneath this hat? Besides the producer's odd choice to wear a bright red bomber jacket, dark jeans and brown boots to the 2014 Grammys, his Vivienne Westwood accessory was, rightfully, the subject of many memes that year.

BEST: Lady Gaga (2010)

Singer Lady GaGa arrives at the 52nd Annual GRAMMY Awards held at the Staples Center.  (Photo by Frank Trapper/Corbis via Getty Images)
(Photo by Frank Trapper/Corbis via Getty Images)

Lady Gaga looked like a modern-day Glinda the Good Witch in this sparkling Armani Privé gown, which she paired with an oversized star she reportedly held all night.

WORST: Alicia Keys (2002)

Alicia Keys during The 44th Annual Grammy Awards at Staples Center in Los Angeles, California, United States. (Photo by Jeff Kravitz/FilmMagic, Inc)
(Photo by Jeff Kravitz/FilmMagic, Inc)

We have so many questions about this 2002 Grammy Awards red carpet disaster, courtesy of Alicia Keys. It’s unclear what she was going for here, but whatever it was, she failed.

Best: Ariana Grande (2020)

LOS ANGELES, CALIFORNIA - JANUARY 26: Ariana Grande arrives at the 62nd Annual GRAMMY Awards at Staples Center on January 26, 2020 in Los Angeles, California. (Photo by Steve Granitz/WireImage)
(Photo by Steve Granitz/WireImage)

Ariana Grande looked like a fairytale princess come to life when she walked the 2020 Grammys red carpet in a grey Giambattista Valli gown.

WORST: Kylie Jenner (2019)

LOS ANGELES, CALIFORNIA - FEBRUARY 10: Kylie Jenner attends the 61st Annual Grammy Awards at Staples Center on February 10, 2019 in Los Angeles, California. (Photo by David Crotty/Patrick McMullan via Getty Images)
(Photo by David Crotty/Patrick McMullan via Getty Images)

Sure, Kylie Jenner might not be a singer, but this Michael Jackson-esque Balmain jumpsuit was so bad we couldn't let it go unpunished.

BEST: Jennifer Lopez (2000)

Jennifer Lopez (Photo by Jeff Vespa/WireImage)
Jennifer Lopez (Photo by Jeff Vespa/WireImage)

Jennifer Lopez's green Versace look at the 2000 Grammy Awards is arguably one of the best red carpet looks of all time. Fun fact: J. Lo reprised this very look during Milan Fashion Week 2019 — and it was just as magical.

WORST: Billie Eilish (2020)

LOS ANGELES, CA - JANUARY 26: Billie Eilish attends the 62nd Annual Grammy Awards at Staples Center on January 26, 2020 in Los Angeles, CA. (Photo by David Crotty/Patrick McMullan via Getty Images)
(Photo by David Crotty/Patrick McMullan via Getty Images)

Billie Eilish's oversized lime green and black Gucci ensemble, glasses and face mask felt more like a disguise than a red carpet-approved look for the 2020 Grammy Awards.

BEST: Selena (1994)

Singer Selena (Quintanilla) receives Grammy Award at The 36th Annual Grammy Awards on March 1, 1994 in New York, New York at Radio City Music Hall. (Photo by Larry Busacca/Getty Images)
(Photo by Larry Busacca/Getty Images)

The late, great Selena Quintanilla took home two Grammys in 1994, including Best Mexican-American Album — a huge milestone for Latin music — and rocked one of the most iconic Grammy looks of all time.

WORST: Avril Lavigne (2003)

Avril Lavigne (Photo by Jim Spellman/WireImage)
Avril Lavigne (Photo by Jim Spellman/WireImage)

Avril Lavigne has never been one to conform to mainstream fashion trends — and we love her for it. Unfortunately, that does not exempt her from making this list with her highly-questionable 2003 Grammys red carpet outfit, complete with a skull and crossbones belt and Converse sneakers.

BEST: Cardi B (2023)

LOS ANGELES, CALIFORNIA - FEBRUARY 05: (FOR EDITORIAL USE ONLY) Cardi B attends the 65th GRAMMY Awards at Crypto.com Arena on February 05, 2023 in Los Angeles, California. (Photo by Axelle/Bauer-Griffin/FilmMagic)
(Photo by Axelle/Bauer-Griffin/FilmMagic)

Cardi B looked like a living piece of art in this royal blue curve-hugging gown designed by Gaurav Gupta for the 2023 Grammys, where she left many fans gagging for more.

WORST: Cher (2008)

LOS ANGELES, CA - FEBRUARY 10:  Singer Cher poses in the press room during the 50th annual Grammy awards held at the Staples Center on February 10, 2008 in Los Angeles, California.  (Photo by Vince Bucci/Getty Images)
(Photo by Vince Bucci/Getty Images)

Cher is a style icon, but her 2008 Grammy Awards dress is a crime against fashion. Why she chose to turn up in a garbage bag is beyond us, but she has already proven countless times since then that she can do much better.

BEST: Ciara (2015)

LOS ANGELES, CA - FEBRUARY 08:  Singer Ciara attends The 57th Annual GRAMMY Awards at the STAPLES Center on February 8, 2015 in Los Angeles, California.  (Photo by Jason Merritt/Getty Images)
(Photo by Jason Merritt/Getty Images)

Ciara looked like a chic black cloud at the 2015 Grammys, with a swooping, ruffled black gown from Alexandre Vauthier.

WORST: Sheryl Crow (2002)

Sheryl Crow during 44th GRAMMY Awards - Arrivals at Staples Center in Los Angeles, California, United States. (Photo by KMazur/WireImage)
(Photo by KMazur/WireImage)

Evidently, 2002 was a difficult year for fashion. "If It Makes You Happy" singer Sheryl Crow walked the red carpet in this plunging, lace-up jumpsuit, with matching cowboy boots, a full-length denim coat and classic early-aughts ombre sunglasses.

BEST: Shania Twain (1999)

Shania Twain (Photo by Jim Smeal/Ron Galella Collection via Getty Images)
(Photo by Jim Smeal/Ron Galella Collection via Getty Images)

Shania Twain rocked this iconic Marc Bouwer dress when she won the awards for Best Country Song and Best Female Country Vocal Performance for "You're Still the One" in 1999. The look was such a standout that in 2022, country singer Kelsea Ballerini borrowed the dress to wear to the Academy Of Country Music Honors.

WORST: Nicki Minaj (2012)

LOS ANGELES, CA - FEBRUARY 12:  Nicki Minaj arrives at The 54th Annual GRAMMY Awards at Staples Center on February 12, 2012 in Los Angeles, California.  (Photo by Steve Granitz/WireImage)
(Photo by Steve Granitz/WireImage)

We're not sure what possessed Nicki Minaj to opt for this bold Versace look on the 2012 red carpet — we're just hoping to never see it again.

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