From 1955 to Now: The Oscar Dresses We Can't Forget (and Don't Want To!)

By InStyle Staff
Updated: Feb 20, 2019 @ 10:35 am
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It's practically a given that any actress who steps foot on the Oscars red carpet will look gorgeous, but only a very special and select few can be called "unforgettable."

Now that the 2018 Oscars ceremony is right around the corner (to air Sunday, March 4, at 8 p.m. ET on ABC), we thought it was the perfect time to dig through the archives and unearth the most extraordinary ensembles we've seen in the 88-year history of the Academy Awards red carpet.

From Marilyn Monroe's cloud of black tulle for the 23rd Academy Awards in 1951 to Lupita Nyong'o's real-life Cinderella moment in a plunging aqua Prada creation in 2014, flash back to the most breathtaking gown to have graced the Oscars red carpet, ever.

VIDEO: The Best Oscars Fashion of All Time

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Marilyn Monroe, 1951

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Marilyn Monroe selected a cloud of black tulle from the 20th Century Fox wardrobe department for the 23rd Annual Academy Awards.
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Grace Kelly, 1955

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Grace Kelly won an Oscar for The Country Girl in a classic ice-blue design by Edith Head. The gown, which was originally created for the movie's premiere, was cut from a bolt of $4,000 French satin and paired with a matching evening coat.

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Uma Thurman, 1995

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Nominated for her role in Pulp Fiction, Uma Thurman opted for a simple lilac design from Prada.
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Nicole Kidman, 1997

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Nicole Kidman made history with her daring chinoiserie gown from Christian Dior.

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Gwyneth Paltrow, 1999

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"I just wanted to look very sweet," Gwyneth Paltrow said of her pretty pink Ralph Lauren gown.

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Cate Blanchett, 1999

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When it came to her stunning bespoke John Galliano gown, Cate Blanchett had a hand in the design process. And, bonus — according to Blanchett, the knit dress (trimmed with Lesage embroidery) was comfortable as well!
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Renee Zellweger, 2001

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This canary vintage Jean Desses gown made Renee Zellweger one to watch on the red carpet.

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Julia Roberts, 2001

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Julia Roberts accepted her Oscar for Erin Brockovich in a dramatic velvet-and-satin vintage Valentino gown from the designer's 1982 collection dedicated to movie stars. Valentino told InStyle, "This dress made me nervous. You are never sure who is going to wear what until they walk out onto the stage. That night I was in Rome, watching the Oscars live on television, and I stayed up until the wee hours of the morning to see if she wore it."

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Charlize Theron, 2000

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Charlize Theron's Vera Wang dress was cut to showcase her incredible shape.
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Kate Winslet, 2002

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Nominated for Iris, English rose Kate Winslet blossomed in scarlet Ben de Lisi. "Kate prefers clothes that don't scream theatrics," the designer told InStyle.

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Reese Witherspoon, 2002

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Reese Witherspoon stole the spotlight at her Academy Awards debut, thanks to a Valentino makeover. "It was her first time presenting and Reese wasn't as established back then," the designer told InStyle. "People thought of her as cute, but not glamorous."

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Cameron Diaz, 2002

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Cameron Diaz belted her floral-print Emanuel Ungaro dress with a 19th-century Indian necklace from Fred Leighton for a look that was uniquely her.
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Jennifer Garner, 2004

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The Valentino gown the designer created for Jennifer Garner took four couturiers more than 300 hours to create, the designer told us.

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Beyoncé, 2005

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Beyoncé made her way down the red carpet in a luscious black velvet vintage gown from Atelier Versace.

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Hilary Swank, 2005

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Her role in Million Dollar Baby gave Hilary Swank the super-toned body for this dare-to-bare Guy Laroche gown.
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Keira Knightley, 2006

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"Keira wanted something dramatic and sexy," Vera Wang told InStyle of the burgundy mermaid dress she made for Knightley's Oscar appearance."The color is absolutely gorgeous on her."

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Michelle Williams, 2006

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Brokeback Mountain nominee Michelle Williams owned the red carpet in a marigold design from Vera Wang. The silk-chiffon dress, chosen a week before the ceremony, was accessorized with dark 19th-century Fred Leighton diamonds.

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Jennifer Lopez, 2007

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Presenter Jennifer Lopez sparkled in a crystal-strung Marchesa design. "Pretty huh? I want to keep it!" she told reporters of the custom gown.
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Marion Cotillard, 2008

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Marion Cotillard shined in this Jean Paul Gaultier embellished gown. "Marion initially requested something simple, but I wanted everyone to see the woman I saw," the designer told InStyle. "So I showed her the sketches for this mermaid-inspired dress, and she loved it. We waited two weeks for the fabric, which was printed with fish scales and laboriously hand-embroidered."

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Freida Pinto, 2009

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Indian actress Freida Pinto gave a nod to her homeland with a sari-inspired design from John Galliano. Complementing the cobalt design (and the theme!) was a 150-year-old diamond from her native country.

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Anne Hathaway, 2009

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Anne Hathaway glowed like a pearl in Giorgio Armani.
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Sandra Bullock, 2010

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"The dress does make the woman," joked Sandra Bullock of her embroidered silver Marchesa gown. Not so! The peek-a-boo design perfectly showcased the star's lithe shape.

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Mila Kunis, 2011

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Mila Kunis looked radiant in a lavender haute couture design from Elie Saab. The only drawback to the chiffon-and-lace layered number? A lack of insulation. "I'm cold, I have to admit!" Kunis joked on the red carpet.

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Angelina Jolie, 2012

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When Angelina Jolie bared her right leg in a stunning velvet Atelier Versace gown, it became an instant internet sensation. Jolie accented the classic gown with Neil Lane jewels, a Jaime Mascaro bag and custom Salvatore Ferragamo velvet peep-toes.
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Gwyneth Paltrow, 2012

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"I've learned to wear what works for my body while always taking a bit of a risk," Gwyneth Paltrow told InStyle of her sleek all-white Tom Ford dress. She accessorized the gown and cape with Anna Hu Haute Joaillerie diamonds, Jimmy Choo shoes, and a sleek low ponytail.

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Jennifer Lawrence, 2013

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Jennifer Lawrence stole the show in a strapless Dior Haute Couture pale blush gown that she styled with Chopard diamonds and a metallic Roger Vivier clutch. The Best Actress winner for Silver Linings Playbook wore pear-shaped white diamond drop earrings, plus a white diamond band, floral diamond ring, and the show-stopping centerpiece: a 74-carat strand of 150 diamond beads, which she wore backwards, draping down her back.

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Lupita Nyong'o, 2014

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Lupita Nyong’o had a real-life Cinderella moment—she took her red carpet stroll in a sweeping deep-plunge Prada gown fit for a princess, complete with Fred Leighton jewelry, including one gold headband (aka tiara).

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Emma Stone, 2015

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Emma Stone embraced chartreuse, aka one of the trickiest shades ever. She stunned in a bead-embroidered Elie Saab gown that featured full sleeves and an open back.

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Lupita Nyong'o, 2015

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With thousands of tiny pearls and a fit that was divine, it’s no surprise that Lupita Nyong'o's Calvin Klein Collection halter dress for the Oscars was later stolen (and returned). 

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Cate Blanchett, 2016

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Blue officially became the color of the night when endorsed by Blanchett and, of course, she chose the most spectacular shade—an icy crystal that picks up the sparkle of her Tiffany & Co. jewels (and also matches the Roger Vivier clutch). Those three-dimensional flowers of her Armani Privé gown added a rare touch of whimsy to the Oscars.

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Jessica Biel, 2017

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Jessica Biel was the very definition of a golden goddess at the 2017 Oscars in a glittering KaufmanFranco gown. And when it came to jewelry, she wasn't afraid to outshine her dress with an extravagant gold, diamond, and platinum necklace from Tiffany's, which is estimated to be worth around $2 million.

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Michelle Williams, 2017

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The actress decided to keep it classic in Louis Vuitton — fitting, considering she's the face of the brand. The simplicity of her dress's black velvet bodice was offset by a heavily-embroidered skirt. Meanwhile, diamond stud earrings and a matching bracelet added the right amount of bling.

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Zendaya, 2018

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Zendaya looked every inch of a leading lady in a whimsical Giambattista Valli gown that elegantly skimmed her lithe frame. A one-sleeve silhouette offered major Grecian vibes, while dangling diamond earrings gave a hint of Old Hollywood.
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Margot Robbie, 2018

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Margot Robbie's Chanel Haute Couture gown for the 2018 Academy Awards took 550 hours to custom create by fourteen hands. The dress's corset bodice features a 3D band of crystals that effortlessly drapes off her shoulders and is supported by two crystal camellias (Coco Chanel's favorite flower.)

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Nicole Kidman, 2018

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Nicole Kidman shut down the 2018 Oscars red carpet in a cobalt blue Armani Privé dress. At first glance, all the attention is drawn to gown's giant bow in the center, but upon closer inspection, a surprise leg reveal is what really made the ensemble a true showstopper.
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