The best Oscar dresses of all time list is ever-evolving, but if there’s one thing for certain these celeb women are always on it. The Oscar’s red carpet always brings some of the most memorable fashion moments of the year. The annual ceremony is a culmination of award season and we look forward to who takes home the coveted statuette, but more importantly, who wears what. Sure, the winners go down in history but we’ll be talking about the best oscar dresses for years to come.
Halle Berry’s iconic 2002 Elie Saab dress immediately comes to mind. Vogue editor Christian Allaire listed Janelle Monae’s 2021 caped Ralph Lauren dress as a fan favorite for the best Oscar dresses of all time. And the vibrant hue of Viola Davis’ green Vera Wang dress against her copper natural fro lives rent-free in my head. We can’t mention fashion without name-dropping Zendaya, whose canary-yellow Valentino Haute Couture dress flowed through the air like her waist-length locks.
As we approach the 94th annual Academy Awards (March 27), we’re looking back at the best Oscar dresses of all time.
11. Billy Porter, 2019 Oscars
In 2019, Oscar’s host and former Pose actor Billy Porter defied gender norms by wearing a Christian Siriano tuxedo gown on the Oscar’s red carpet. In a piece published on Vogue, Porter revealed he always wanted to wear a ball gown and was inspired by the genderless models at Palomo Spain’s fashion show that same year. As for working with Siriano, the campy style star wrote,
“I’ve always wanted to work with [Siriano]. I got this Oscars gig [hosting a red carpet pre-show], and at his party after the show, I just dropped it in his ear and said, “Do you think you’d have time to make me a gown?” And he said, “AAAAA-BSOLUTELY.”
10. Zendaya, 2015 Oscars
Zendaya famously wore faux locs on the 2015 Oscars red carpet to compliment her silk off-the-shoulder Vivienne Westwood dress that made headlines on mostly everyone’s best-dressed list. The fashion icon, styled by Law Roach, became the talk of the award season after her stunning appearance and controversial comments by former E! host Giuliana Rancic infamously joked that she looked like she smelled like “smells like patchouli oil or weed.”
Reflecting on the incident in 2021, Zendaya says the offensive comment is how “change happens,” She added, “And it made me think, ‘How could I always have a lasting impact on what people saw and associated with People of Color?’”
It’s safe to say she’s left a lasting fashion impression and has many more carpets to go!
9. Taraji P. Henson, 2017 Oscars
In 2017, Taraji P. Henson attended the Academy Awards wearing a custom off-the-shoulder Alberta Ferretti gown with a daring thigh-high split making her the belle of the ball. Henson’s Hidden Figures co-star Octavia Spencer was nominated for “Best Supporting Actress” while the film garnered a “Best Picture” and “Best Adaptive Screenplay” nomination. While Moonlight took home the trophy at the end of the night, Taraji was the big winner of the night in this dress!
8. Janelle Monae, 2020 Oscars
Janelle Monae gave us a hooded moment on the 2020 Oscars red carpet in a sparkling Ralph Lauren look that was a fresh take on the traditional red carpet gown. Monae’s dramatic sequin two-piece instantly placed her in the ranks of Oscar’s best dresses of all time. According to WWD journalist Booth Moore, who tweeted, “The custom crystal silk lame tulle mesh dress with draped hood has 600 hours worth of hand embroidery and 168,000 Swarovski crystals. #Oscars”
7. Debbie Allen, 1982 Oscars
With a bold thigh-high split, shoulders pads, and dazzling fringe, Debbie Allen’s Oscar’s dress was the best of 80s fashion combined for a gown that always makes the best Oscar dresses list. That year, Allen performed alongside Gregory Hines bringing not only her spectacular moves but a timeless look that could easily be worn on the carpet today.
6. Lupita N’yongo, 2014 Oscars
Lupita Nyong’o took home the Oscar’s statue, in 2014, for “Best Supporting Actress” for her critically-acclaimed role in her debut feature film 12 Years A Slave. The melanated actress looked like Cinderella in a custom Prada gown that won over viewers’ hearts. Celebrity stylist Micaela Erlanger completed the look with a matching Prada clutch and platforms, Fred Leighton jewels, and a stunning crystal headband.
5. Zendaya, 2021 Oscars
Zendaya doesn’t miss. Period. In 2021, Zendaya and her longtime stylist Law Roach collaborated on a look that instantly became one of the best Oscar dresses of all time. Zendaya wore a fun strapless yellow Valentino cutout gown that flowed with every step. To complete the look, she wore a matching mask, which she took off on the carpet, Jimmy Choos, and over 183 carats of Bulgari diamonds, valued at over $6 million.
4. Diana Ross, 1982 Oscars
Diana Ross served glitz and glamour at the 1982 Oscars in a red sequin gown with fringe detail and white fur stole that stole the show. Ross was photoed waltzing the red carpet with Ernest Thompson.
3. Viola Davis, 2012 Oscars
With The Help a fan favorite that year, “Best Actress” nominee Viola Davis wore this gorgeous emerald Vera Wang gown and her natural copper tresses to the red carpet that left us green with envy. In a controversial upset, Davis lost that year but won over the fashion gawds, big time!
2. Diahann Carroll, 1969 Oscars
If perfection had an image, Diahann Carroll’s 1969 Oscar’s dress would be the reference photo. The ethereal gown with sparkling sheer overlay brought Carroll’s signature glamorous style to the Oscar’s stage where she presented Stanely Kubrick the “Special Effects” award for his film 2001: A Space Odyssey. Kubrick won, but sis had “special” on lock.
1. Halle Berry, 2002
When it comes to best, iconic, and memorable Oscar gowns, Halle Berry’s 2002 Elie Saab dress is at the top of the list. The floral-embroidered, sheer bodice and burgundy silk creation was the perfect gown for a historic night. Berry became the first Black woman to win “Best Actress,” at the 74th Academy Awards, for her role in Monster’s Ball.
Despite kicking open the door for other Black actresses to follow in her footsteps, Berry revealed she fell victim to the “Oscar’s curse.” In a 2020 interview with Variety, Halle Berry referred to the win as one of her biggest heartbreaks.
“I think it’s largely because there was no place for someone like me,” she said. “I thought, ‘Oh, all these great scripts are going to come my way; these great directors are going to be banging on my door.’ It didn’t happen. It actually got a little harder. They call it the Oscar curse. You’re expected to turn in award-worthy performances.”These days, Berry is in front and behind the lens — starring and directing her films. Her 2021 Netflix film Bruised garnered favorable reviews proving the iconic actress has plenty of more iconic red carpet moments up her sleeve…or lack thereof.RELATED STORIES:
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