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When people talk about the best (and worst) Oscar dresses of all time, certain gowns consistently come up. One of those dresses is the floor-length pink Ralph Lauren taffeta gown that Gwyneth Paltrow famously wore to the 71st annual Academy Awards on March 21, 1999, where she won her career-defining Best Actress award for her performance in Shakespeare In Love. The in-your-face pink dress, with its V-neck bodice and tiny spaghetti straps, hung loosely on Paltrow’s body and billowed out into a wide skirt. At the time, the bubblegum-hued dress received mixed reviews from fashion watchers (even her mother, Blythe Danner, was said to hate it) and it famously divided as many people back then as it still does today.

“It’s a funny story because it was in the days before stylists,” Paltrow said in a 2021 interview with Vogue, where she revisited some of her most iconic looks. “I had been looking through the Ralph Lauren lookbook and in the [New York Fashion Week catwalk] show, they’d had this pink bubblegum taffeta skirt, and I was, like, that’s very me. So I called and I said, ‘Can I borrow this for the Oscars?’ And they said, ‘We’d like to make you something,’ which was thrilling. And so they made me this beautiful dress, and I love it and I kept it and I have it.”

That quick recollection of her most famous red carpet look is accurate; however, Paltrow did leave out a few key details of the story. Ready to take a trip down memory lane and revisit Paltrow’s iconic pink Ralph Lauren gown? Read on for the full story of the much-loved and much-hated taffeta gown, and find out how it helped cement Paltrow’s ’90s style icon status.

Shakespeare in Love, starring Gwyneth Paltrow, Joseph Fiennes, Geoffrey Rush, Colin Firth, Ben Affleck and Judi Dench, was a lighthearted and clever imagining of how William Shakespeare’s play Romeo and Juliet came to be written and produced. Directed by John Madden and written by Marc Norman and Tom Stoppard, the movie satirizes theatre life and plays with what is both known and unknown about Shakespeare’s life and Elizabethan times.

The film was released in North American theatres by Miramax on December 11, 1998, winning rave reviews and box-office success. In fact, the film would become the ninth-highest-grossing film of 1998, ultimately grossing $289 million worldwide. As expected, accolades followed the film’s box office success, and at the beginning of 1999, Shakespeare In Love received 13 Academy Award nominations for the upcoming 71st Academy Awards.

Paltrow was nominated for Best Actress and, of course, needed a dress to wear to the festivities. It would be her second time attending the Oscars. Previously, she had received praise when she wore a simple Calvin Klein bias-cut slip dress when she attended the 68th annual Academy Awards on March 25, 1996.

Paltrow famously didn’t work with a stylist when searching for a dress to wear to the 1999 Oscars, but the lesser-known part of the story is that she was being actively wooed by different designers in the lead-up to the big night. Calvin Klein, Donna Karan and Giorgio Armani, among others, were all offering to dress Paltrow, according to Bronwyn Cosgrave’s 2007 book Made for Each Other: Fashion and the Academy Awards. In fact, in the lead-up to the awards, as Paltrow settled into the luxury hotel Shutters on the Beach in Santa Monica – a kind of ground zero for Operation Dress – she was torn between a metallic Armani and an icy blue Celine. While she was debating between the two, she fell in love with a bubblegum-pink taffeta skirt seen in Ralph Lauren’s seasonal lookbook.

The skirt that Paltrow fell in love with was part of Ralph Lauren’s spring/summer 1999 collection, which was shown on the runway in New York in November 1998. The unsuspecting skirt appeared towards the end of the runway show on a model who was also wearing a cotton pink tank top and shrunken zip hoodie. The show wasn’t exactly a runway success. In fact, at the time, the New York Times called the collection a disappointment “filled with nice but quite ordinary-looking sportswear.”

Still, the floor-length pink taffeta skirt from the spring/summer 1999 collection captured Paltrow’s attention. She called Ralph Lauren and asked to borrow it…and the label offered to make her a gown instead.

“Gwyneth wanted one-of-a-kind. Originally she was interested in a two-piece situation,” a West Coast PR rep for Ralph Lauren told Cosgrave. “Then she decided on a gown – to go even more formal.… It was definitely all about pink.”

But there was still uncertainty in the days before the Oscar ceremony: “We would go to Shutters for fittings – many, many fittings – and run into representatives from Armani and Celine,” the PR rep recalled.

According to reports, Paltrow didn’t want to put too much pressure on herself and simply wanted to “look really sweet.”

“I worked with their celebrity liaison, which was a new thing.… All these brands were getting these celebrity PR people to help get women like me in their dresses,” Paltrow recalled in the In Vogue: The 90s documentary. “We ideated this dress all together and then that was that. The pink-bubblegum ballgown dress was born.”

Paltrow did ultimately settle on the custom Ralph Lauren dress, with some last-minute alterations. The corset-like bustier of the dress was removed, which resulted in a looser style that gave the gown just a hint of 1990s grunge. Ironically, it’s the fit of the dress that tops the list of reasons of why people don’t like the dress – Paltrow’s own mother included. Blythe Danner told Us years later: “It didn’t fit her very well.”

The 71st annual Academy Awards took place on March 21, 1999, at the Dorothy Chandler Pavilion in Los Angeles. Paltrow was nominated for Best Actress for her role as Viola de Lesseps, up against Cate Blanchett (for Elizabeth), Fernanda Montenegro (Central Station), Meryl Streep (One True Thing) and Emily Watson (Hilary and Jackie). Paltrow wasn’t the frontrunner that night – Blanchett was – but all eyes were on Paltrow. After all, at this point she was a ’90s minimalist style icon.

“They say I was, like, a definitive ’90s style lady…which…at the time I just thought I was wearing, you know, minimalist stuff with brown lip liner and a lot of powder,” Paltrow told Vogue.

Paltrow spent Oscar day with her mother getting ready at Shutters. Kevyn Aucoin (her favourite makeup artist) plucked her eyebrows and blushed her cheeks while hairstylist Orlando Pita smoothed her hair into a Grace Kelly-style chignon. Then she made a final choice about her gown, at the last minute veering between the Celine two-piece and the pink Ralph Lauren gown.

When she stepped out on the red carpet, on the arm of her adored dad, heads turned.

With her blonde hair pulled back, Paltrow appeared on the red carpet making her biggest fashion statement to date with the pink princess gown. She wore the dress with a matching pink shawl, a pair of pink Manolo Blahnik strappy sandals and accessorized with Harry Winston jewellery: a 40-carat diamond necklace, bracelet and pair of earrings valued at around US$160,000.

On the red carpet, Paltrow told a reporter: “If you think about how much people are talking about something as silly as a dress, I think it would make me absolutely incapable of leaving the house. So I just tuned it all out and wore what I thought was pretty.”

Pretty in pink was surprisingly one of the night’s biggest trends – thanks to Paltrow, Geena Davis and Rachel Griffiths – but Paltrow captured everyone’s attention with her loose-fitting Ralph Lauren frock.

Fashion commentators were divided in opinion that night. TV Guide.com recounts one critic saying that Paltrow looked like “a Barbie doll wrapped in satin ribbon,” while another commentator called it “incongruous with the current fashion” but “suitable Gwyneth Paltrow.” Interestingly, pioneer of award show red carpet coverage Joan Rivers actually liked the dress, comparing Paltrow’s look that night to Grace Kelly…a comparison that has been repeated at length throughout the years.

But back to the criticisms. One of the biggest criticisms that night, which is still echoed today by critics, was that the Ralph Lauren dress was a little loose on top. The rumour is that after the last fitting, Paltrow removed some light padding from the bustier of the dress herself and then called Lauren to tell him what she had done – unfortunately, there was no time left for another adjustment. However, no one in either the designer’s or the actress’s camp has ever been willing to corroborate (or deny) that rumour.

Paltrow ultimately won the Best Actress Oscar at the 71st Academy Awards, which was presented to her by Jack Nicholson. Her win was a surprise that night, as was her fumbling acceptance speech. (Paltrow claims that she doesn’t remember giving her speech that night, and says that she has never watched it.) As for Shakespeare in Love, the film ultimately won the most Oscars that night, seven out of 13 nominations: Best Picture (controversially defeating critically favoured Saving Private Ryan and becoming the first comedy to win the award since the 1977 film Annie Hall), Best Actress (Paltrow), Best Supporting Actress (Dench), Best Screenplay Written Directly for the Screen, Best Original Musical or Comedy Score, Best Art Direction and Best Costume Design.

“It was a pretty intense time in my life. I was only 26; there was a lot going on,” recalled Paltrow in the In Vogue: The 90s documentary.

After the big night
Paltrow made headlines around the globe not only for her surprise win, but for her custom-made pink taffeta Ralph Lauren gown. Throughout the years that followed, the look would consistently pop up on both sides of Oscar fashion history, being hailed as both one of the best and the worst Oscar dresses of all time.

As time passed, and Paltrow further cemented her status as a style icon, the affinity for the dress has changed, with many critics now praising the dress, and Paltrow, for bringing pink back into fashion at a time when dark and dreary grunge aesthetics were dominating the fashion landscape. The simplicity of the cut – and even the loose-fitting bust – has somehow stood the test of time and become a symbol of everything that was iconic of that fashion era.

The dress is also part of the beginning of a radical change in celebrity fashion. It was not only the beginning of labels actively courting actresses for the red carpet, but also in many ways represents the beginning of a new era of the red carpet fashion.

“When certain actresses started to take a much more, frankly exciting and more of the moment fashion choices, that’s when the world started to look at the red carpet in a very different way,” said Anna Wintour in the In Vogue: The 90s documentary.

What about the extravagant jewels Paltrow wore for her unexpected Oscar win? Turns out her father, the late director and producer Bruce Paltrow, later purchased the Harry Winston jewellery she had borrowed to wear with her pink Ralph Lauren dress the night she won the Oscar. “After I won, my dad, as a present, surprised me with them,” she revealed to Vogue.

Her father died in 2002, and Paltrow described how she wore the jewels when she married Brad Falchuk on September 29, 2018, in the Hamptons, to include and remember her father on that day.

The dress remains Paltrow’s most memorable look, a look she still has in her closet today. She briefly slipped back into the dress in 2023 when she wore it for the first time in over two decades while drinking Champagne, and dabbing on bright red blush in a festive holiday ad that was posted on Goop’s Instagram.

“It’s so funny. Who would have thought a dress would be a famous thing…but I have it. She’s with me,” Paltrow said of the dress in the In Vogue: The 90s documentary.

Here’s hoping that won’t be the last we see of the bubblegum-pink Ralph Lauren dress. Paltrow told The Hollywood Reporter that she is hoping it will get its time to shine once again with her daughter, Apple, explaining: “Maybe she’ll wear it to prom and do a Pretty in Pink thing and resew it and cut it up.”

Want more? You can read other stories from our The Story Of series, including the white Tom Ford gown and cape Paltrow wore to the 2012 Oscars, right here.