Celebs' First Oscars Dress: Then VS Now

In 1996, Halle Berry wasn’t yet a household name, and she made her first appearance at the Academy Awards in a lavender dress that was oh so ‘90s. It was silk and satin at the same time with a draped scarf to match. Her signature short haircut was perfectly on trend for the time and while the dress may be a bit dated, it’s still quite pretty. In 2017, Berry had clearly come into her own and looked incredible even two decades later. While her one shoulder custom Atelier Versace gown was gorgeous, the star of the night was her hair, which was worn in a natural curly afro style.

Jennifer Aniston has been a red carpet fixture since she began starring on “Friends” in the mid ‘90s, and yet it took until 2006 for her to attend her first Academy Awards ceremony. The actress debuted in a style that she would become known for: simple, classic, and black. This dress was by Rochas and featured a timeless silhouette and a train. In 2017, when she was acting as a presenter at the ceremony, she wore a much more daring shape, opting for a plunging neckline as well as a thigh high slit. You go, Jen!

Jennifer Garner looked thrilled to be at the 2003 Oscars after starring in “Catch Me If You Can” with Leonardo DiCaprio the previous year. While her icy blue Versace dress was the perfect choice for a newcomer, her irrepressible smile was what made the outfit. In 2018, the star made it onto most of the best dressed lists after wearing this striking royal blue gown, which was also by Versace. It featured a caped design as well as some complex draping that made it look even more noteworthy from the back.

This actress has an ethereal beauty that will always be timeless. At the 1999 Oscars, Cate Blanchett took home the statue for Best Actress for her role as Queen Elizabeth I in “Elizabeth”. For the occasion, she chose a nearly sheer custom John Galliano dress with detailed embroidery on the back, including flowers and even a hummingbird. Blanchett’s style has only evolved since then, and in 2016 she stunned on the red carpet in a light green gown by Armani Prive,which also featured plenty of embellishment that took the form of applique flowers.

Can you believe that back in 2011 we were barely familiar with Jennifer Lawrence’s hilarious irreverent humor? When she made her Oscars red carpet debut, fashion insiders perked up because while her bright red Calvin Klein gown was simple, flawlessly executed and quickly skyrocketed her into the sartorial elite. By 2018, the Oscars were old hat for her, and she went with a more edgy rocker style, pairing her chainmail style dress, which was designed by Dior, with tousled waves and a dark winged eye look. It’s hard to choose which dress we love more!

#5: Kate Winslet

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One might assume that Kate Winslet went to her first Academy Awards after starring in the blockbuster film “Titanic”, but she was actually nominated in the Best Supporting Actress category even earlier for her role in “Sense and Sensibility”. She went all out in a fun pink Vivienne Westwood gown. Many Oscars ceremonies later, she walked the red carpet on the arm of her “Titanic” costar, Leonardo DiCaprio, in 2016. In a much more grown up look, she chose a gleaming black Ralph Lauren gown that had a somewhat futuristic appearance.

#4: Lupita Nyong'o

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Lupita Nyong'o’s first time at the Academy Awards was relatively recently, in 2014, when she was nominated for Best Supporting Actress for her role in “12 Years a Slave”. Not only did she take home the award, but she also piqued the interest of style watchers everywhere after she twirled on the red carpet in a Grecian style pastel blue gown by Prada. In 2018, she appeared with her “Black Panther” costars and opted for a custom atelier Versace dress that made her look more like a warrior than a damsel in distress.

While we now can hardly imagine a red carpet without Julia Roberts’s presence, she was a relative Hollywood newcomer in 1990 when she came to the ceremony with Kiefer Sutherland after being nominated for her role in “Steel Magnolias”. She looked somewhat unsure of herself in a shapeless taupe dress. But in 2019, she was the picture of confidence when she took to the stage to present the biggest award of the night- for Best Picture. Her electric pink gown was by Elie Saab and showed that she was definitely no longer a wallflower.

After starring in “Atonement”, Irish actress Saoirse Ronan was nominated for an Academy Award when she was just 13 years old. She attended the ceremony in a kelly green dress (perhaps a nod to her ancestral heritage?) with her hair pulled back in a simple ponytail and looked perfectly age appropriate. By 2018 though, she had really come into her own, and looked much more self assured in a pale pink Calvin Klein gown that looked like a simple column from the front, but featured an oversized bow on the back.

The Oscars were decidedly more casual in the early ‘90s when Nicole Kidman walked the red carpet for the first time as part of a major Hollywood power couple with then-husband Tom Cruise. Her dress was short, black and simple, and she even wore dark nylons, which you’d likely never see at the Academy Awards today. But by 2018, she was making our jaws drop in a stunning architectural electric blue gown with an oversized bow. While she may not have been nominated that year, she certainly received the award for Best Dressed from many fashion industry insiders.