The Story Behind Gwyneth Paltrow's Famous Oscars Dress, And How Her Wearing It Put Ralph Lauren In A Tizzy

Gwyneth Paltrow in Shakespeare in Love.
(Image credit: Universal Pictures)

These days Gwyneth Paltrow is more likely to be seen going topless in an Instagram cooking video than getting all dressed up for the red carpet, but she’s still provided some memorable moments in celebrity fashion over the years. One of her more notable looks was from the 1999 Academy Awards, where she won the Best Actress Oscar for Shakespeare in Love. She turned heads in that pink Ralph Lauren gown that night, but apparently the designer was quite displeased.

A new book about the Se7en star is out, titled Gwyneth: The Biography by Amy Odell. In it, the author discusses all aspects of the actress’s life after conducting more than 220 interviews. In one section, Odell explores the drama surrounding the 1999 Oscars dress that was inspired by Grace Kelly:

Gwyneth Paltrow wears a pink Ralph Lauren dress to the 71st Annual Academy Awards in 1999.

(Image credit: Photo by Ke.Mazur/WireImage)

Ralph Lauren was reportedly asked to design Gwyneth Paltrow’s dress for the awards, but the designer apparently became “frustrated” with the actress, Odell writes (via People), when the dress required multiple alterations due to Paltrow's continued weight loss. An excerpt from Gwyneth: The Biography reads:

Leading up to the awards, she hadn’t been eating much and kept losing weight, necessitating extra fittings, where Gwyneth asked the Ralph Lauren team in New York to bring the neckline lower and lower. Lauren became so frustrated that he didn’t want to send the dress back to Los Angeles. But his team convinced him, and found a skilled seamstress to fit the pieces of the dress onto Gwyneth there.

It’s wild that Ralph Lauren allegedly wanted to back out of working with the actress, and things didn’t get better for the designer on the night of the awards. The biography continues:

The designers at Ralph Lauren noticed that something looked off when she wore it that night. The fabric was puckering, a little wrinkly, loose around her torso — as if she had instantly lost 10 pounds. They realized she hadn’t worn the inner detachable corset that came with the gown, which would have made it fit more snugly. Lauren was not happy about the fit.

I’m not sure what happened to the corset, but looking back at the photo, it does appear that the dress was loose-fitting.

The book excerpt doesn’t specify what became of the Ralph Lauren design, but we do know that her 2000 Academy Award dress was given to charity. As for her other iconic outfits — like the sheer look Millie Bobby Brown copied earlier this year — Gwyneth Paltrow saves a lot of clothes for her daughter Apple, because we all know those ‘90s styles are coming back. Apple even modeled her mom’s “goth” Oscars dress from 2002.

While others enjoy her looks of yesteryear, it seems the actress is more comfortable shedding her top altogether, as she's shared topless sunbathing pics as well as celebrated her birthdays in her birthday suit.

Ralph Lauren may not have had the best experience, but either way, it’s good to see Gwyneth Paltrow feeling so good in her skin — red carpet dress or not.

Heidi Venable
Content Producer

Heidi Venable is a Content Producer for CinemaBlend, a mom of two and a hard-core '90s kid. She started freelancing for CinemaBlend in 2020 and officially came on board in 2021. Her job entails writing news stories and TV reactions from some of her favorite prime-time shows like Grey's Anatomy and The Bachelor. She graduated from Louisiana Tech University with a degree in Journalism and worked in the newspaper industry for almost two decades in multiple roles including Sports Editor, Page Designer and Online Editor. Unprovoked, will quote Friends in any situation. Thrives on New Orleans Saints football, The West Wing and taco trucks.

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