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24 best and worst Oscars red carpet looks of all time, from Michelle Yeoh to Björk - Yahoo Canada Shine On

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Celebrities like Lady Gaga, Nicole Kidman and Halle Berry are no strangers to the Oscars red carpet. (Photos via Getty Images)
Celebrities like Lady Gaga, Nicole Kidman and Halle Berry are no strangers to the Oscars red carpet. (Photos via Getty Images)

This year's Oscars are officially around the corner, as some of Hollywood's biggest celebrities prepare for a night of glitz and glamour at the Dolby Theatre in Los Angeles. The 95th Annual Academy Awards is set to air Sunday, March 12 at 8 p.m. ET/5 p.m. PT.

For his third time in the role, Jimmy Kimmel is prepping to host the star-studded ceremony — and he's made it clear he'll accept no funny business. In a recent interview, the comedian and TV host referenced last year's "Oscars Slap," joking that he'd "beat the s— out of" anyone who tries to slap him this year.

Kimmel also gave a "guarantee" that this year's telecast will run longer than before, since the Academy of Motion Picture Arts and Sciences decided to air all nominated categories as opposed to last year.

With some of the year's biggest blockbuster films up for awards, such as "Avatar: The Way of Water," "Elvis" and "Top Gun: Maverick," it's clear this year's red carpet will be full of A-list stars wearing some of fashion's most well-known designers.

In anticipation for the 95th Academy Awards, we're looking back at some of the best and worst fashion choices made on the Oscars red carpet over the years.

BEST: Michelle Yeoh (2019)

Michelle Yeoh looked regal at the 91st Oscars in 2019. (Rick Rowell via Getty Images)
Michelle Yeoh looked regal at the 91st Oscars in 2019. (Rick Rowell via Getty Images)

If you look up the definition of "elegance," Michelle Yeoh will be the first icon that comes up. But seriously, the "Everything Everywhere All at Once" star's off-the-shoulder Elie Saab gown for the 91st Oscars shined with beauty.

WORST: Uma Thurman (2004)

Uma Thurman missed the mark at the 76th Academy Awards in 2004. (Photo by Jeffrey Mayer/WireImage)
Uma Thurman missed the mark at the 76th Academy Awards in 2004. (Photo by Jeffrey Mayer/WireImage)

Uma Thurman might turn heads anywhere she goes, but for the 76th Oscars, the attention was for all the wrong reasons. The "Kill Bill" actress has cited wearing this Christian Lacroix design as her "most embarrassing experience."

BEST: Cate Blanchett (2016)

Cate Blanchett looked stunning in floral at the 88th Oscars in 2016. (Photo by Steve Granitz/WireImage)
Cate Blanchett looked stunning in floral at the 88th Oscars in 2016. (Photo by Steve Granitz/WireImage)

When it comes to the Oscars red carpet, Cate Blanchett never misses. The "Tár" actress proved that at the 88th Academy Awards wearing a seafoam green Armani Prive gown with floral embellishments.

WORST: Jennifer Hudson (2007)

Jennifer Hudson's metallic bolero held her back on the red carpet at 2007's 79th Oscars. (Photo by John Shearer/WireImage)
Jennifer Hudson's metallic bolero held her back on the red carpet at 2007's 79th Oscars. (Photo by John Shearer/WireImage)

Jennifer Hudson didn't look her sharpest at the 79th Academy Awards. But at least the "Dreamgirls" star ditched the metallic bolero to let her Oscar de la Renta gown shine after she won Best Supporting Actress that year.

BEST: Timothée Chalamet (2022)

Timothée Chalamet proved that going shirtless can still be chic at the 94th Academy Awards 2022. (Photo credit should read P. Lehman/Future Publishing via Getty Images)
Timothée Chalamet proved that going shirtless can still be chic at the 94th Academy Awards 2022. (Photo credit should read P. Lehman/Future Publishing via Getty Images)

Say what you want about Timothée Chalamet, but his shirtless Louis Vuitton look at the 94th Oscars was full-on chic. Not many stars can perfectly rock an embroidered lace tuxedo jacket with lace trim detailing, along with sharply-fitted trousers.

WORST: Timothée Chalamet (2020)

Timothée Chalamet didn't serve his best red carpet look at the 92nd Oscars in 2020. (Rick Rowell via Getty Images)
Timothée Chalamet didn't serve his best red carpet look at the 92nd Oscars in 2020. (Rick Rowell via Getty Images)

But don't get us wrong: Chalamet has had his fair share of red carpet misses. For the 92nd Oscars, the "Dune" star stepped out wearing a navy blue Prada getup that could either pass as a paramedic's uniform or a costume for the live-action version of "Paw Patrol."

BEST: Jennifer Lopez (2003)

Jennifer Lopez looked like a regal mermaid at the 75th Academy Awards in 2003. (Photo by J. Vespa/WireImage)
Jennifer Lopez looked like a regal mermaid at the 75th Academy Awards in 2003. (Photo by J. Vespa/WireImage)

Can you really call it a red carpet if Jenny From the Block doesn't make an appearance? Jennifer Lopez's mint-green sari-style Valentino gown for the 75th Oscars looked like she was draped in elegant water.

WORST: Björk (2001)

Björk certainly stirred conversations after her red carpet appearance at the 73rd Oscars in 2001. (Photo by Jeffrey Mayer/WireImage)
Björk certainly stirred conversations after her red carpet appearance at the 73rd Oscars in 2001. (Photo by Jeffrey Mayer/WireImage)

Björk's "swan dress," crafted by Marjan Pejoski, is probably the most iconic look ever seen at an Oscars red carpet, but not in a good way. While walking the event, the Icelandic singer even stopped several times to "lay eggs" in front of bewildered spectators. Still, the artist leaned into the criticism, noting that her look was a joke intended to "take the piss" out of the event.

BEST: Halle Berry (2002)

Halle Berry remains an iconic star after her 2002 look at the 74th Oscars. (Photo by SGranitz/WireImage)
Halle Berry remains an iconic star after her 2002 look at the 74th Oscars. (Photo by SGranitz/WireImage)

If you're at all familiar with the internet, it's likely you've seen the iconic clip of Halle Berry becoming the first woman of colour to win Best Actress for her work in "Monster's Ball." Wearing an intricately embroidered Elie Saab gown for the 74th Oscars, Berry looked like a winner before even stepping into the venue.

WORST: Lady Gaga (2015)

Lady Gaga must've helped the kitchen staff at the 87th Oscars before walking the red carpet in 2015. (Photo by Jason Merritt/Getty Images)
Lady Gaga must've helped the kitchen staff at the 87th Oscars before walking the red carpet in 2015. (Photo by Jason Merritt/Getty Images)

We definitely love a major fashion moment by Lady Gaga, but her look for the 87th Oscars did not serve glamour. With a gown created by Paris-based designer Azzedine Alaia, the "House of Gucci" actress was the subject of countless memes thanks to huge red gloves that look like she just finished a shift at her dishwashing gig.

BEST: Jessica Chastain (2022)

Jessica Chastain channelled the camp aura of Tammy Faye for the 94th Oscars in 2022. (Photo by P. Lehman/Future Publishing via Getty Images)
Jessica Chastain channelled the camp aura of Tammy Faye for the 94th Oscars in 2022. (Photo by P. Lehman/Future Publishing via Getty Images)

Bordering on the edge of stunning and tacky, Jessica Chastain sharply channelled the flamboyant nature of her "Eyes of Tammy Faye" character for the 94th Oscars. The colourful Gucci gown was seemingly the right choice, as the star took home the Best Actress award that night.

WORST: Michelle Williams (2017)

Even Michelle Williams couldn't make a bathing suit look elegant at the 89th Oscars in 2017. (Photo by Dan MacMedan/Getty Images)
Even Michelle Williams couldn't make a bathing suit look elegant at the 89th Oscars in 2017. (Photo by Dan MacMedan/Getty Images)

Michelle Williams is no doubt an icon, but her 89th Oscars red carpet screams the opposite of stardom. Styled by Kate Young, the Louis Vuitton outfit makes the "Fabelmans" actress look like she ditched the beach, covering her plunging black swimsuit with the best piece of fabric she could find.

BEST: Angela Bassett (2019)

Angela Bassett was the centre of attention at the 91st Academy Awards in 2019. (Photo by Jeff Kravitz/FilmMagic)
Angela Bassett was the centre of attention at the 91st Academy Awards in 2019. (Photo by Jeff Kravitz/FilmMagic)

Add this stunning look to whatever makes the list of "Angela Bassett did the thing." The "Black Panther" actress stepped onto the 91st Oscars red carpet rocking a vibrant, one-shouldered fuchsia gown created by Reem Acra.

WORST: Halle Berry (2021)

Halle Berry was serving Edna Mode on the 93rd Oscars red carpet in 2021. (Photo by Chris Pizzello-Pool/Getty Images)
Halle Berry was serving Edna Mode on the 93rd Oscars red carpet in 2021. (Photo by Chris Pizzello-Pool/Getty Images)

Likened to Edna Mode from "The Incredibles" and Johnny Depp in "Willy Wonka and the Chocolate Factory," Halle Berry bore the brunt of many jokes at the 93rd Oscars. While the "Moonfall" star's fresh haircut was the worst part of her look, the mauve strapless Dolce & Gabbana gown was just as messy.

BEST: Lupita Nyong'o (2014)

Lupita Nyong'o looked like Cinderella at the 86th Oscars in 2014. (Photo by Dan MacMedan/WireImage)
Lupita Nyong'o looked like Cinderella at the 86th Oscars in 2014. (Photo by Dan MacMedan/WireImage)

It's too difficult to count how many times "Cinderella" has been made into a movie, but the gown Lupita Nyong'o wore at the 86th Oscars proves the world could use one more adaptation. Coloured in "Nairobi blue" to honour the city she grew up in, the "Black Panther" actress looked purely regal in Prada.

WORST: Jamie Lee Curtis (2004)

Jamie Lee Curtis was ready for a live-action film version of
Jamie Lee Curtis was ready for a live-action film version of "The Sims" at the 76th Oscars in 2004. (Photo by David LEFRANC/Gamma-Rapho via Getty Images)

Jamie Lee Curtis might be "Hollywood royalty," but the "Everything Everywhere All at Once" actress is also the queen of looking like a Sim on the red carpet. Curtis's strapless blue gown for the 76th Oscars, designed by Monique L'Huillier, is all the proof that's needed.

BEST: Kodi Smit-McPhee (2022)

Kodi Smit-McPhee rocked an aquamarine tuxedo at the 94th Oscars in 2022. (Photo by Angela Weiss / AFP via Getty Images)
Kodi Smit-McPhee rocked an aquamarine tuxedo at the 94th Oscars in 2022. (Photo by Angela Weiss / AFP via Getty Images)

Kodi Smit-McPhee channelled masculine elegance at the 94th Oscars. The "Power of the Dog" actor stepped onto the red carpet wearing an aquamarine double-breasted custom tuxedo, courtesy of Bottega Veneta.

WORST: Faith Hill (2001)

Faith Hill went full-on rainbow at the 74th Academy Awards in 2002. (Frank Micelotta/ImageDirect)
Faith Hill went full-on rainbow at the 74th Academy Awards in 2002. (Frank Micelotta/ImageDirect)

Vibrancy should definitely make more of an appearance on red carpets, but it'd be understandable why some star's are afraid of going rainbow-brite at major events. Faith Hill's Versace gown at the 74th Oscars was unfortunately a red carpet eyesore.

BEST: Lily James (2022)

Lily James mixed sexy and sweet for the 94th Academy Awards in 2022. (Photo by P. Lehman/Future Publishing via Getty Images)
Lily James mixed sexy and sweet for the 94th Academy Awards in 2022. (Photo by P. Lehman/Future Publishing via Getty Images)

Lily James perfectly blended Versace's sexiness with the softness of a princess at the 94th Academy Awards. On the red carpet, the "Pam & Tommy" star stunned wearing a baby pink flowing gown embroidered with glittering floral embellishments.

WORST: Tyra Banks (2000)

Tyra Banks failed to make purple taffeta work at the 72nd Oscars in 2000. (Photo by SGranitz/WireImage)
Tyra Banks failed to make purple taffeta work at the 72nd Oscars in 2000. (Photo by SGranitz/WireImage)

Tyra Banks might've been going for an aesthetic that'd match her character in "Life-Size," but the purple taffeta on her Vera Wang gown at the 72nd Oscars was difficult to make cute.

BEST: Angelina Jolie (2004)

Angelina Jolie looked angelic at the 76th Academy Awards in 2004. (Photo by Bill Davila/FilmMagic)
Angelina Jolie looked angelic at the 76th Academy Awards in 2004. (Photo by Bill Davila/FilmMagic)

When you think of regal beauty, how can you not think of Angelina Jolie? For the 76th Oscars, the "Those Who Wish Me Dead" actress looked angelic wearing a satin white gown designed by Marc Bouwer.

WORST: Gwyneth Paltrow (2002)

Gwyneth Paltrow herself admitted her
Gwyneth Paltrow herself admitted her "goth" gown at the 74th Oscars in 2002 could've used some work. (Photo by SGranitz/WireImage)

You can't blame us: Gwyneth Paltrow herself admitted her Alexander McQueen gown for the 74th Oscars was a wrong move. Writing on her website Goop in 2017, the "Iron Man" actress shared that the "goth" look had "a few issues."

BEST: Ariana DeBose (2022)

Ariana DeBose looked like the warmest star at the 94th Academy Awards in 2022. (Photo by P. Lehman/Future Publishing via Getty Images)
Ariana DeBose looked like the warmest star at the 94th Academy Awards in 2022. (Photo by P. Lehman/Future Publishing via Getty Images)

Ariana DeBose encapsulated her entire energy into one look for the 94th Oscars. The "West Side Story" actress rocked a "punchy" red Valentino outfit at the event that made her beam with confidence.

WORST: Cher (1986)

Cher went bold with her porcupine look at the 58th Oscars in 1986. (Photo by LGI Stock/Corbis/VCG via Getty Images)
Cher went bold with her porcupine look at the 58th Oscars in 1986. (Photo by LGI Stock/Corbis/VCG via Getty Images)

Cher's revealing Bob Mackie outfit for the 58th Oscars was a bit too sharp — in all the wrong ways. The singer and actress tried channelling her inner show-girl, but the all-black look skewed too far into porcupine region.

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