A Comprehensive List of the Most Stylish Oscar Dress the Year You Were Born

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The first ever Oscars began in 1929, and almost 100 years later it still happens! (Although the academy still is snubning women and various nominees, but that is a completely different topic.) With nine decades worth red carpets, that means there have been SO many stylish dresses and gowns that have adorned them. Here we look back at some of the most amazing, fashion-forward-looking for each year that goes all the way back to ’29. (Wow, these black and white photos are a relapse!) From Lupita Nyong’o to Penelope Cruz and from Audrey Hepburn to Grace Kelly, click through to see the most stylish Oscar dress the year you were born.

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Gemma Chan, 2019

That Crazy rich Asians star wore a voluminous Valentino dress with a high collar on the red carpet and landed on best dressed list. As a bonus, the dress even had pockets !!!

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Viola Davis, 2018

Viola put on a pink sequin Michael Kors dress and gained access to a matching clutch and sparkling earrings in 2018. She won the Oscar for Best Supporting Actress the year before for her emotional performance in Fenceand presented the award for Best Supporting Actor to Sam Rockwell this year.

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Naomie Harris, 2017

That Moonlight star was nominated for best supporting actress this year and she did not play any game on the red carpet. This white sequin Calvin Klein mini became jaw-dropping – especially when paired with her bold yellow heels.

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Cate Blanchett, 2016

Sure, Cate Banchett’s Armani Prive dress might have been a little divisive, but we were all in this gorge-watercolor, feathery details and Swarovski crystals. It was definitely a winning look since she took the award for Best Actress for her work in Carol.

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Zendaya, 2015

She absolutely glowed in this neutral Vivienne Westwood off-the-shoulder dress. She wore her hair in locs, which provoked some controversial remarks from Giuliana Rancic. Zendaya then posted a strong statement about the hairstyle on her Instagram, and Rancic later apologized for her insensitive comments.

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Lupita Nyong’o, 2014

Lupita blew everyone away with his performance in 12 years slavese– she took the award for best supporting actress tonight. Her Prada dress was definitely the most stylish on the red carpet thanks to its simple silhouette, subtle sheen and dramatic train.

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Zoe Saldana, 2013

This couture Alexis Mabille dress seemed like it had a lot to do – The floral appliqués! The belt at the waist! The Ombre train! – but due to the neutral colors and the sleek design, it was the most stylish of the night. That same year she appeared in Star Trek Into the Dark.

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Emma Stone, 2012

This fuchsia Giambattista Valli dress with a cinched waist and dramatic pussy bow was such a stunning in 2012. She handed out the award for best visual effects with Ben Stiller later on stage.

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Jennifer Lawrence, 2011

Fresh from his breakout role in Winter legs, JLaw looked so chic on the red carpet in this simple Calvin Klein dress and tousled hair. She received her first nomination for Best Actor this year.

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Sandra Bullock, 2010

The actress shone in this mermaid dress paired with slim, straight hair and a bright red lip. She won her long-awaited Oscar for Best Actress in The blind side that evening.

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Taraji P.Henson, 2009

Taraji made an unforgettable Oscar debut in a strapless Roberto Cavalli number, short bob and dazzling necklace. She received her first nomination for Best Supporting Actress The curious case of Benjamin Button.

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Marion Cotillard, 2008

Marion literally wore a mermaid dress on the red carpet. She looked brilliant in this Jean Paul Gaultier dress that had a golden scale-like pattern. She grew to international fame that year after her breakout role as Édith Piaf in La Vie en Rosewho earned her the award for Best Actress.

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Penelope Cruz, 2007

The actor brought greater volume to the red carpet in a red-blue Versace dress with a wrinkled train and tight-fitting top. She finished off the look with a slim bun, statement earrings and a small clutch.

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Reese Witherspoon, 2006

Reese won the fashion game (and an Oscar for Best Actress!) When she appeared in this lovely Dior judge with beaded embellishments and a low-cut neckline. She won the award later that night for her performance in Go on the line.

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Hilary Swank, 2005

Who could ever forget this daring Guy Laroche dress? The actress nailed her shoulder bags on the red carpet that night to emphasize the backless number. She also won the Oscar for Best Actress for her role in Million Dollar Baby.

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Angelina Jolie, 2004

Angie stunned in this silky cream-colored halter dress, and let’s be right: only she could make a coordinating shawl THIS glam. She certainly channeled old Hollywood style into this classic look.

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Jennifer Lopez, 2003

J. Lo killed the red carpet in this mint green Valentino dress with a shoulder and pearls at the bottom. She attended the awards with her then-boyfriend Ben Affleck. (#TBT to Gigli.)

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Halle Berry, 2002

You can not think of the Oscars in 2002 without also imagining this Elie Saab dress on Halle Berry. It remains one of the actor’s most iconic looks of all time, thanks to its completely transparent top and strategically placed floral embroidery.

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Julia Roberts, 2001

The actor was all elegance in this vintage black and white Valentino dress and pinned-up ‘do. Her amazing performance in Erin Brockovich earned her the award for Best Actress for the Night.

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Salma Hayek, 2000

Salma brought early agitated glam to the ceremony in a diving purple halter dress and matching shawl. She handed out the Oscar for technical achievement later that evening.

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Celine Dion, 1999

One word: unforgettable. Celine knew how to talk about the red carpet that year when she wore the blazer on her all-white Dior suit backwards and was given accessories with a pointed hat and sunglasses (note: the ceremony was held in the evening). She performed with Andrea Bocelli at the ceremony.

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Sharon Stone, 1998

Sharon is not here to follow the standard rules for red carpet. The actor was wearing a satin Vera Wang skirt combined with a white shirt with button from Gap. However, this is not the first time she sees a high-low look at the red carpet. Her 1996 Oscar attire literally included a black Gap roll collar.

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Nicole Kidman, 1997

Leave it to Nicole Kidman to perform then husband Tom Cruise in a silky chartreuse John Galliano Dior dress paired with an adorable mini bag. So on trend!

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Elizabeth Shue, 1996

This candidate for best actress dazzled in a sultry white pillar and accessory with a diamond necklace on the red carpet.

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Oprah, 1995

Oprah played this monochrome ensemble and ogle-worthy diamonds the same year she was named the richest woman in entertainment. Honestly, goal.

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Sharon Stone, 1994

The dramatic veil and the whimsical brooch only made this large number more memorable. Sharon went on to hand out the award for best costume design later that evening.

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Cindy Crawford, 1993

The model’s skin-tight bandage dress highlighted her figure as she adorned the red carpet with then-husband Richard Gere, who was the presenter that evening.

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Demi Moore, 1992

Demi left the red carpet on fire in this low-cut purple dress with matching shawls and gloves. She starred in A couple of good men, which was nominated for Best Picture that year.

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Madonna, 1991

The singer channeled Marilyn Monroe in this Bob Mackie gown and a cluster of Harry Winston accessories. She also sang a hungry performance of her song “Sooner or Later” at the ceremony.

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Michelle Pfeiffer, 1990

Michelle’s navy blue dress, pearls and (inexplicable) flowers in her hand were a sight to behold. She rocked Oscar that year with a nomination for Best Actress in The Fabulous Baker Boys.

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Associate Fashion Editor
I’m Cosmopolitan’s Associate Fashion Editor and write about all the trends, big celeb fashion moments, and why wide jeans are basically the best.
Mili is a cosmopolitan intern who loves all things fashion, beauty and pop culture.

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