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The first-ever Oscars began in 1929, and almost 100 years later it’s still happening! (Even if the Academy is still snubbing women and diverse nominees, but that’s a whole other issue.) With nine decades worth of red carpets, that means there have been SO many stylish dresses and gowns that have graced them. Here, we’re taking a look back at some of the most stunning, fashion-forward ones for each year dating all the way back to ’29. (Wow, those black-and-white pics are a throwback!) From Lupita Nyong’o to Penelope Cruz and from Audrey Hepburn to Grace Kelly, click through to see the most stylish Oscars dress the year you were born.
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Gemma Chan, 2019
The Crazy Rich Asians star wore a voluminous Valentino dress with a high collar to the red carpet and landed on the best-dressed list. As a bonus, the frock even had pockets!!!
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Viola Davis, 2018
Viola donned a bright pink sequin Michael Kors gown and accessorized with a matching clutch and sparkly hoop earrings in 2018. She won the Best Supporting Actress Oscar the previous year for her emotional performance in Fences, and presented the award for Best Supporting Actor to Sam Rockwell this year.
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Naomie Harris, 2017
The Moonlight star was nominated for Best Supporting Actress this year, and she didn’t play any games on the red carpet. This white sequin Calvin Klein mini was jaw-dropping—especially when paired with her bold yellow heels.
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Cate Blanchett, 2016
Sure, Cate Banchett’s Armani Prive gown might’ve been a little divisive, but we totally stan this gorge aqua hue, feathery details, and Swarovski crystals. It was clearly a winning look since she picked up the Best Actress Award for her work in Carol.
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Zendaya, 2015
She absolutely glowed in this neutral off-the-shoulder Vivienne Westwood dress. She wore her hair in locs, which stirred up some controversial remarks from Giuliana Rancic. Zendaya then posted a powerful 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 her performance in 12 Years a Slave—she picked up the Best Supporting Actress award this evening. Her Prada gown was definitely the most stylish on the red carpet, thanks to its simple silhouette, subtle shimmer, and dramatic train.
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Zoe Saldana, 2013
This couture Alexis Mabille gown seemed like it had a lot going on—The floral appliques! The belted waist! The ombre train!—but because of the neutral colors and sleek design, it was the most stylish of the night. This same year she appeared in Star Trek Into Darkness.
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Emma Stone, 2012
This fuchsia Giambattista Valli gown featuring a cinched waist and dramatic pussybow was such a stunner in 2012. She presented the award for Best Visual Effects with Ben Stiller later on stage.
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Jennifer Lawrence, 2011
Fresh off her breakout role in Winter’s Bone, JLaw looked so chic on the red carpet in this simple Calvin Klein gown and tousled hair. She received her first Best Actress nomination this year.
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Sandra Bullock, 2010
The actress shined in this mermaid gown paired with sleek, straight hair and a bright red lip. She won her long-awaited Oscar for Best Actress in The Blind Side that night.
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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 Best Supporting Actress nomination for The Curious Case of Benjamin Button.
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Marion Cotillard, 2008
Marion wore a mermaid dress to the red carpet in the most literal sense. She looked radiant in this Jean Paul Gaultier gown that featured a golden scale-like pattern. She grew to international fame that year after her breakout role as Édith Piaf in La Vie en Rose, which earned her the Best Actress award.
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Penelope Cruz, 2007
The actress brought major volume to the red carpet in a blush pink Versace gown with a ruffled train and tight-fitting bodice. She finished off the look with a sleek bun, statement stud 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 showed up in this lovely Dior dumber with beaded embellishments and a low-cut neckline. She won the award later that night for her performance in Walk the Line.
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Hilary Swank, 2005
Who could ever forget this daring Guy Laroche dress? The actress nailed her over-the-shoulder poses on the red carpet that night to emphasize the backless number. She also picked up the Best Actress Oscar 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 real: Only she could make a coordinating shawl THIS glam. She definitely channeled old Hollywood style in this classic look.
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Jennifer Lopez, 2003
J. Lo killed the red carpet in this mint green one-shoulder Valentino dress with beading at the hem. She attended the awards with her then boyfriend Ben Affleck. (#TBT to Gigli.)
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Halle Berry, 2002
You can’t think of the 2002 Academy Awards without also envisioning this Elie Saab dress on Halle Berry. It remains one of the actress’s most iconic looks of all time thanks to the completely see-through bodice and the strategically-placed floral embroidery.
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Julia Roberts, 2001
The actress was all elegance in this vintage black-and-white Valentino dress and pinned-up ‘do. Her stellar performance in Erin Brockovich earned her the Best Actress award for the night.
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Salma Hayek, 2000
Salma brought early-aughts glam to the ceremony in a plunging lilac halter dress and matching shawl. She presented the Academy Award for Technical Achievement later that night.
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Celine Dion, 1999
One word: UNFORGETTABLE. Celine knew how to be the talk of the red carpet that year when she wore the blazer on her all-white Dior suit backwards, and accessorized with a pointed hat and sunglasses (note: the ceremony was held in the evening). She performed along side Andrea Bocelli at the ceremony.
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Sharon Stone, 1998
Sharon is not here to follow standard red-carpet rules. The actress wore a satin Vera Wang skirt combined with a white button-down shirt from the Gap. This isn’t the first time she sported a high-low look on the red carpet though. Her 1996 Oscar outfit literally included a black Gap turtleneck.
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Nicole Kidman, 1997
Leave it to Nicole Kidman to upstage 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 Best Actress nominee dazzled in a sultry white column and accessorized with a diamond necklace on the red carpet.
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Oprah, 1995
Oprah sported this monochrome ensemble and ogle-worthy diamonds the same year she was named the richest woman in entertainment. Honestly, goals.
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Sharon Stone, 1994
The dramatic veil and whimsical brooch only made this sheer number more memorable. Sharon went to present the award for Best Costume Design later that night.
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Cindy Crawford, 1993
The model’s skin-tight bandage dress accentuated her figure as she graced the red carpet with then-husband Richard Gere, who was a presenter that evening.
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Demi Moore, 1992
Demi left the red carpet ablaze in this low-cut lilac dress with matching shawl and gloves. She co-starred in A Few 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 sung a sultry performance of her song “Sooner or Later” at the ceremony.
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Michelle Pfeiffer, 1990
Michelle’s navy blue gown, pearls and (inexplicable) flowers in hand were a vision of grace. She rocked the Oscar’s 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 any and all trends, major celeb fashion moments, and why wide-leg jeans are basically the best.
Mili is a Cosmopolitan intern who loves all things fashion, beauty, and pop culture.
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