Grammys 2025: Best and worst red carpet looks of all time, from Jennifer Lopez to Ariana Grande — vote on your fashion picks

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

Celebrities like Jennifer Lopez, Justin Bieber, Ariana Grande, Blac Chyna and Britney Spears had some of the best and worst looks at the Grammys of all time. (Photos via Getty Images; illustration by Yahoo Canada)
Celebrities like Jennifer Lopez, Justin Bieber, Ariana Grande, Blac Chyna and Britney Spears had some of the best and worst looks at the Grammys of all time. (Photos via Getty Images; illustration by Yahoo Canada)

Music's biggest night is just about here, with the 2025 Grammys set to be the first awards ceremony to air since the Los Angeles wildfires broke out. Some of the entertainment industry's biggest names — from Beyoncé and Taylor Swift, to Sabrina Carpenter and Chappell Roan — are planning to make appearances on the event's red carpet.

The 67th Grammy Awards will air live from the Crypto.com Arena in Los Angeles on Sunday, Feb. 2, 2025 at 8 p.m. ET/5 p.m. PT. For the fifth time in a row, Trevor Noah will host the ceremony, but this year's event will focus on supporting local relief efforts.

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. Over the years, we've seen a range of stunning looks and head-scratching fashion on the Grammys red carpet.

So, we're asking you, Yahoo Canada readers: Which were the best and worst red carpet looks ever seen on the Grammys red carpet? Vote below, see what readers picked last year and check out some of the most eye-catching looks stars have worn in the past.

For last year's 66th Grammy Awards, Yahoo Canada readers were pretty dead set on their picks for best and worst dressed.

Out of more than 17,000 votes, 48 per cent of people voted for Kelly Clarkson as the best-dressed celebrity at the event when put up against Dua Lipa, Janelle Monae, Olivia Rodrigo and Halle Bailey. On the other hand, 47 per cent of more than 15,000 voters chose Miley Cyrus as worst dressed over Doja Cat, Fantasia Barrino, Taylor Swift and Ice Spice.

LOS ANGELES, CALIFORNIA - FEBRUARY 04: (FOR EDITORIAL USE ONLY) Kelly Clarkson attends the 66th GRAMMY Awards at Crypto.com Arena on February 04, 2024 in Los Angeles, California. (Photo by Axelle/Bauer-Griffin/FilmMagic)
Kelly Clarkson at the 2024 Grammy Awards in Los Angeles on Feb. 4. (Photo by Axelle/Bauer-Griffin/FilmMagic)

Kelly Clarkson was a class act during last year's Grammy Awards. The 42-year-old singer stunned wearing an off-the-shoulder ivory gown featuring a subtle mermaid hem. The custom Jason Wu Collection garment was paired with matching white clutch and Jared Atelier diamonds reportedly worth more than $200,000.

The talk show host also brought along her eight-year-old son, Remington, as her date for the evening. The three-time Grammy winner was nominated for best pop vocal album for Chemistry, a collection of songs written after her split from ex-husband Brandon Blackstock. However, the award went to Swift's album Midnights.

LOS ANGELES, CALIFORNIA - FEBRUARY 04: (FOR EDITORIAL USE ONLY) Miley Cyrus attends the 66th GRAMMY Awards at Crypto.com Arena on February 04, 2024 in Los Angeles, California. (Photo by Axelle/Bauer-Griffin/FilmMagic)
Miley Cyrus at the 2024 Grammy Awards in Los Angeles on Feb. 4. (Photo by Axelle/Bauer-Griffin/FilmMagic)

On the other hand, Miley Cyrus was considered the worst-dressed star on last year's Grammys red carpet. The 32-year-old singer turned heads as she stepped out wearing nothing but 14,000 gold safety pins. Her hair was styled in a Farah Fawcett-style bouffant, while the dress — which took "675 hours of meticulous work" by fashion house Maison Margiela — channelled a 1920s flapper and Egyptian goddess aesthetic.

While the artist might've gotten questionable looks for the outfit she wore on the red carpet, she was one of the true winners of the night. Cyrus won her first-ever Grammy Award for for best pop solo performance for mega-hit "Flowers."

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


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)
SZA at the 2018 Grammy Awards in New York City on Jan. 28. (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.

Kelly Osbourne at the 2011 Grammy Awards in Los Angeles on Feb. 13. (Photo by Kevin Mazur/WireImage)
Kelly Osbourne at the 2011 Grammy Awards in Los Angeles on Feb. 13. (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.

LOS ANGELES, CALIFORNIA - FEBRUARY 04: (FOR EDITORIAL USE ONLY) Olivia Rodrigo attends the 66th GRAMMY Awards at Crypto.com Arena on February 04, 2024 in Los Angeles, California. (Photo by Lionel Hahn/Getty Images)
Olivia Rodrigo at the 2024 Grammy Awards in Los Angeles on Feb. 4. (Photo by Lionel Hahn/Getty Images)

Olivia Rodrigo took home her first-ever Grammy Award for best new artist at the 2022 ceremony, and has been on an upward trajectory ever since. At the 2024 Grammys, the "Drivers License" artist wowed in a vintage Versace gown that was first worn by Linda Evangelista in 1995.

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.

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)
Dua Lipa at the 2021 Grammys in Los Angeles on March 14. (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.

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.

LOS ANGELES, CA - FEBRUARY 12:  Singer Beyonce, winner of Best Urban Contemporary Album for 'Lemonade' and Best Music Video for 'Formation,' poses in the press room during The 59th GRAMMY Awards at STAPLES Center on February 12, 2017 in Los Angeles, California.  (Photo by Frederick M. Brown/Getty Images)
Beyoncé at the 2017 Grammys in Los Angeles on Feb. 12. (Photo by Frederick M. Brown/Getty Images)

Let's be honest, we could make an entire gallery of the best Beyoncé Grammy red carpet looks. The "Cowboy Carter" artist's 2017 look might technically be a press room photo after she won her two awards and skipped the red carpet that year. However, the stunning ruby red sequin gown by Peter Dundas she wore that year — complete by showing off her baby bump while she was pregnant with twins Sir and Rumi — easily shows why she's Queen Bey.

LOS ANGELES, CALIFORNIA - FEBRUARY 04: (FOR EDITORIAL USE ONLY) Halle Bailey attends the 66th GRAMMY Awards at Crypto.com Arena on February 04, 2024 in Los Angeles, California. (Photo by Lionel Hahn/Getty Images)
Halle Bailey at the 2024 Grammys in Los Angeles on Feb. 4. (Photo by Lionel Hahn/Getty Images)

Halle Bailey look like a star at the 2024 Grammys, wearing a plunging crystal-covered neckline gown custom made by Gucci. The "Angel" singer was nominated for best R&B song that year, and sparkled at the event to prove she'd be a worthy winner.

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

Charli xcx went for a white and pink menswear-inspired outfit for the red carpet at the 2015 Grammys, a look that leaves us cringing for the English singer. Attending for her two nominations for "Fancy" with Iggy Azalea, Charli xcx accessorized her white suit with a pink bowtie and fur shawl.

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)
Justin Bieber at the 2022 Grammys in Las Vegas on April 3. (Photo by Jeff Kravitz/FilmMagic)

Justin Bieber's oversized Balenciaga suit and platform monster Crocs definitely made a statement on the red carpet. However, the unusual look left many fans confused by the fashion choices that year.

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)
Mariah Carey at the 1991 Grammys in New York City on Feb. 20. (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, signifying the birth of an iconic diva — both in music and on the red carpet.

LOS ANGELES, CALIFORNIA - FEBRUARY 05: (FOR EDITORIAL USE ONLY) Blac Chyna attends the 65th GRAMMY Awards on February 05, 2023 in Los Angeles, California. (Photo by Jeff Kravitz/FilmMagic)
Blac Chyna at the 2023 Grammys in Los Angeles on Feb. 5. (Photo by Jeff Kravitz/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.

Britney Spears at the Staples Center in Los Angeles, California (Photo by Kevin Mazur/WireImage)
Britney Spears 2000 Grammys in Los Angeles on Feb. 23. (Photo by Kevin Mazur/WireImage)

Britney Spears channelled Old Hollywood glamour at the 2000 Grammy Awards with this stunning winter white look. That year, the "Oops!...I Did It Again" singer was up for best new artist and female pop vocal performance. where she was up for Best New Artist and Female Pop Vocal Performance.

LOS ANGELES, CA - JANUARY 26:  Singer Pharrell attends the 56th GRAMMY Awards at Staples Center on January 26, 2014 in Los Angeles, California.  (Photo by Lester Cohen/WireImage)
Pharrell at the 2014 Grammys in Los Angeles on Jan. 26. (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.

Singer Lady GaGa arrives at the 52nd Annual GRAMMY Awards held at the Staples Center.  (Photo by Frank Trapper/Corbis via Getty Images)
Lady Gaga at the 2010 Grammys in Los Angeles on Jan. 31. (Photo by Frank Trapper/Corbis via Getty Images)

Lady Gaga looked like Glinda the Good Witch from Wicked in this sparkling Armani Privé gown, which she paired with an oversized star she reportedly held all night. The "Bad Romance" singer won two awards that night, including best dance recording and best electronic/dance album, and gave her first-ever performance at the awards show alongside Elton John.

Alicia Keys during The 44th Annual Grammy Awards at Staples Center in Los Angeles, California, United States. (Photo by Jeff Kravitz/FilmMagic, Inc)
Alicia Keys at the 2002 Grammys in Los Angeles on Feb. 27. (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, the "If I Ain't Got You" singer failed. Still, she won a stunning five awards that night, including best new artist, song of the year, best female R&B vocal performance, best R&B song and best R&B album.

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)
Ariana Grande at the 2020 Grammys in Los Angeles on Jan. 26. (Photo by Steve Granitz/WireImage)

Ariana Grande looked like a real-life fairytale princess when she walked the 2020 Grammys red carpet in a grey Giambattista Valli gown. She had been nominated for album of the year, record of the year, best pop solo performance, best pop duo/group performance and best pop vocal album.

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)
Kylie Jenner at the 2019 Grammys in Los Angeles on Feb. 10. (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.

Jennifer Lopez (Photo by Jeff Vespa/WireImage)
Jennifer Lopez at the 2000 Grammys in Los Angeles on Feb. 23. (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.

LOS ANGELES, CALIFORNIA - FEBRUARY 04: (FOR EDITORIAL USE ONLY) Taylor Swift attends the 66th GRAMMY Awards at Crypto.com Arena on February 04, 2024 in Los Angeles, California. (Photo by Axelle/Bauer-Griffin/FilmMagic)
Taylor Swift at the 2024 Grammys in Los Angeles on Feb. 4. (Photo by Axelle/Bauer-Griffin/FilmMagic)

Taylor Swift stepped out in a custom Schiaparelli gown for the 2024 Grammys, one that resembled a bath towel accessorized with with unnecessary long black glove. Still, the "Fortnight" singer won big that night, making history with a fourth album of the year win for "Midnights."

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)
Selena Quintanilla at the 1994 Grammys in New York City on March 1. (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.

Avril Lavigne at the 2003 Grammys in New York City on Feb. 23. (Photo by Jim Spellman/WireImage)
Avril Lavigne at the 2003 Grammys in New York City on Feb. 23. (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 worst-dressed list with her highly-questionable 2003 Grammys red carpet outfit, complete with a skull and crossbones belt as well as Converse sneakers.

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)
Cardi B at the 2023 Grammys in Los Angeles on Feb. 5. (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.

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)
Cher at the 2008 Grammys in Los Angeles on Feb. 10. (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 what looks like a torn-up garbage bag is beyond us. Still, she's since proven countless times that she can do much better.

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)
Ciara at the 2015 Grammys in Los Angeles on Feb. 8. (Photo by Jason Merritt/Getty Images)

Ciara looked like a chic black cloud at the 2015 Grammys. The Alexandre Vauthier black gown she wore featured a swooping, ruffled design full of drama and beauty.

Sheryl Crow during 44th GRAMMY Awards - Arrivals at Staples Center in Los Angeles, California, United States. (Photo by KMazur/WireImage)
Sheryl Crow at the 2002 Grammys in Los Angeles on Feb. 27. (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.

Shania Twain at the 1999 Grammys in Los Angeles on Feb. 24. (Photo by Jim Smeal/Ron Galella Collection via Getty Images)
Shania Twain at the 1999 Grammys in Los Angeles on Feb. 24. (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.

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)
Nicki Minaj at the 2012 Grammys in Los Angeles on Feb. 12. (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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