Grammys 2023: 25 of the best, worst and weirdest Grammys red carpet looks of all time

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 2023 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. The 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 65th Grammy Awards will be airing live from Los Angeles's Crypto.com Arena on Sunday, Feb. 5, 2023 7:00 p.m. EST, with Trevor Noah once again taking up hosting duties.

The star-studded show is set to include performances by Harry Styles, Lizzo, Sam Smith and more.

Ahead of this year's awards, we're looking back at some of the biggest fashion hits and misses from the Grammy red carpet. Scroll through to see if your favourite celebrity's Grammys ensemble made our best or worst list.

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: Cee Lo 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 this Marvel villain reject look was one look 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)

Lipa brought the glamour in a Cher-inspired look by Versace that featured a bejewelled butterfly bodice and thigh-high slit.

WORST: Pink (2002)

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

Pink hit the 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 (2008)

Singer Beyonce Knowles arrives on the red carpet during the 50th Annual GRAMMY�� Awards at the Staples Center, in Los Angeles. Dress by Elie Saab. (Photo by Frank Trapper/Corbis via Getty Images)
(Photo by Frank Trapper/Corbis via Getty Images)

Let's be honest- we could make an entire gallery of the best Beyoncé Grammy red carpet looks. However, this ice blue and silver Elie Saab gown is one unforgettable gown that proves why Bey is the queen of the Grammys.

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)

Bieber's oversized suit and platform 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)

This powerhouse vocalist 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: Madonna (2015)

LOS ANGELES, CA - FEBRUARY 08:  Singer Madonna arrives at the 57th GRAMMY Awards at Staples Center on February 8, 2015 in Los Angeles, California.  (Photo by Jon Kopaloff/FilmMagic)
(Photo by Jon Kopaloff/FilmMagic)

Madonna hit the red carpet of the 2015 Grammy Awards in a matador-inspired ensemble by Givenchy that featured thigh-high leather boots, gloves and a whole lot of sequins.

BEST: Selena Gomez & Taylor Swift (2016)

LOS ANGELES, CA - FEBRUARY 15:  Selena Gomez and Taylor Swift arrives at the The 58th GRAMMY Awards at Staples Center on February 15, 2016 in Los Angeles City.  (Photo by Steve Granitz/WireImage)
(Photo by Steve Granitz/WireImage)

BFFs Selena Gomez and Taylor Swift turned heads as they walked the red carpet together in 2016, with Gomez in a sparkling Calvin Klein gown and Swift in a two-piece custom Versace look.

WORST: Cardi B (2019)

LOS ANGELES, CALIFORNIA - FEBRUARY 10: Cardi B arrives at the 61st Annual GRAMMY Awards at Staples Center on February 10, 2019 in Los Angeles, California. (Photo by Steve Granitz/WireImage)
(Photo by Steve Granitz/WireImage)

Cardi B's vintage Mugler clam-inspired gown looked too much like a costume for one of the biggest nights in music.

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 that 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 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, 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 in 2020, 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)

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 red carpet outfit, complete with a skull and crossbones belt and Converse sneakers.

BEST: Rihanna (2015)

LOS ANGELES, CA - FEBRUARY 08:  Singer Rihanna arrives at the 57th GRAMMY Awards at Staples Center on February 8, 2015 in Los Angeles, California.  (Photo by Jon Kopaloff/FilmMagic)
(Photo by Jon Kopaloff/FilmMagic)

While the “Work” singer has served us countless jaw-dropping red carpet looks over the years, her bright pink Giambattista Valli gown from the 2015 Grammy Awards is most certainly one for the books.

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: Britney Spears (2000)

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

Britney Spears did not come to play at the 2000 Grammy Awards! The queen of pop stunned in this timeless, white gown paired with a matching white, fur stole and diamond necklace — a truly unforgettable look.

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. The “If It Makes You Happy” singer walked the red carpet in this plunging, lace-up jumpsuit, with matching cowboy boots, a full-length denim coat and classic early-2000s 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.” 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 - we're just hoping to never see it again.

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)

The. "Good Days" singer wowed on the 2018 Grammy red carpet wearing this unique, ethereal, fairy-esque gown by Atelier Versace, leaving fans in awe of absolutely striking beauty and fashion sense.

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