The 1999 Oscars Red Carpet’s Most Memorable Style Moments

The Oscars red carpet has been home to so many iconic fashion moments over the years.

The 1999 award show, held at the Dorothy Chandler Pavilion in Los Angeles, was no exception. Two of the most iconic Academy Awards outfits made their debut that year.

First, there was Gwyneth Paltrow’s baby pink spaghetti-strap gown by designer Ralph Lauren. The dress itself, made of a crisp taffeta, wasn’t extremely extravagant. It featured no beading or embellishments, but thanks to its full skirt, it still delivered on the drama.

When Paltrow accepted the Academy Award for Actress in a Leading Role wearing that dress, it became instantly iconic and continues to be one of the most memorable in Oscars history.

Then there was Céline Dion’s unique take on a classic. The singer arrived on the red carpet wearing a white suit by John Galliano, but her jacket was on backward. At the time, she definitely landed on some worst-dressed lists, but we just like to think the “My Heart Will Go On” songstress was way ahead of her time.

“When I wore that, everyone was wearing dresses, not pants,” Dion told People magazine in 2017. “I was the only one with pants in a backward suit from Galliano and if I would do this today it would work. It was avant-garde at the time. And it doesn’t matter, you just have to assume what you wear, you wear, and I did.”

Ahead of this year’s ceremony, which airs on Sunday, Feb. 24 at 8 p.m. Eastern, relive those two iconic style moments and more ― like Ellen DeGeneres’ and Anne Heche’s matching tiny sunglasses, Cate Blanchett’s sheer Galliano gown, and Goldie Hawn’s sparkling blue dress ― below.

Drew Barrymore and Ed Norton

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Joan Rivers

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Gwyneth Paltrow

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Celine Dion

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Ben Affleck and Matt Damon

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Mariah Carey

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Geena Davis

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Jennifer Lopez

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Rachel Griffiths

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Warren Beatty and Annette Bening

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Uma Thurman

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Meryl Streep

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Sophia Loren

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Kim Basinger and Alec Baldwin

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Judi Dench

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Kathy Bates

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Liv Tyler

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Carole Bayer Sager

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Andie MacDowell

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Catherine Zeta-Jones

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Lisa Kudrow

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Helen Hunt

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Anne Heche and Ellen DeGeneres

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Goldie Hawn

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Anjelica Huston

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Tom Hanks and Rita Wilson

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Christina Ricci

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Cate Blanchett

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Renee Zellweger

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Billy Bob Thornton and Laura Dern

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Roberto Benigni and Nicoletta Braschi

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