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“For the entire evening, big-jawed Paltrow, with her nasal, teeth-clenching Lisa Kudrow style, looks like a Green Bay Packers cheesehead tottering atop a mushy pink Hostess cupcake.”
The first Oscar gown I can remember loving was the one Gwyneth Paltrow wore the night she accepted Best Actress for 1998’s Shakespeare in Love. Sitting in my elementary school’s computer room the morning after the ceremony, I sketched it out to show my best friend. It makes sense: The pink Ralph Lauren look was almost designed to appeal to an eight-year-old. The V-neck bodice was held up by tiny spaghetti straps, hung loosely on Gwyneth’s chest, and billowed out into a wide skirt. She carried a gossamer scarf purely for decorative purposes. And it was pink! Like, so fucking pink. It was a dress for a princess, and, holy shit, I loved it.
In 1999, Gwyneth looked like a walking fantasy. But these days it’s more like a fantasy than ever before. The actress told the New York Times in October 2017 that she was among the women who had been sexually harassed by Harvey Weinstein. In the online version of the Times report, there’s even a photo of her from the 1999 Oscars, smiling and holding her gold statue. And printed right above: “I was expected to keep the secret.” The bubblegum taffeta, the picture of innocence, is symbolic of that secret.
Long before, Gwyneth said of the now-iconic Oscars look: “I just wanted to look very sweet.” Made sense: Shakespeare in Love as a whole could be described that way — very sweet. Gwyneth plays the earnest theater lover who defies cultural norms by trying out for one of the bard’s productions. No women allowed, she does her best take on drag. The film portrays a swoony, charming version of 16th-century England — nothing like the arguably more authentic heretic burning in Elizabeth, which starred Gwyneth’s fellow Best Actress nominee Cate Blanchett.
According to the book Made for Each Other: Fashion and the Academy Awards, Gwyneth didn’t work with a stylist, but that didn’t mean designers weren’t clamoring to have her wear their attire. The Ralph slid in at the 11th hour — she visited the boutique days prior the event — and it won largely because of how feminine it looked. During the lead-up to the big night, Gwyneth was at the Shutters on the Beach hotel in Santa Monica with her mom, Blythe Danner, and some friends. She had already collected a Golden Globe and a SAG Award. “When you are with your girlfriends, and you try on this pretty pink dress, and you think it is so great, so pretty,” Gwyneth said. She ditched the bustier that was originally affixed in favor of comfort and a looser style that gave the ensemble just a hint of 1990s grunge.
Even before the dress made its debut, derision followed Gwyneth. At the Independent Spirit Awards, Illeana Douglas reportedly quipped that Harvey and Bob Weinstein weren’t there because they were “pressing Gwynnie’s dress.” Though it reads entirely more sinister in retrospect, it was then a reference to the hyperaggressive campaign the brothers were running for the film. Shakespeare in Love’s Best Picture win has long been seen as one of the more undeserved in Academy history, simply because of Weinstein’s nasty tactics that helped it achieve victory over Saving Private Ryan. “Gwynnie’s” innocent look could have indeed been meant to keep her out of the fray.
But reactions to the gown were immediately divided. In Entertainment Weekly’s style recap, the fashion critics surveyed cooed over it (“Fantastic!” “Perfect!”), while the omniscient voice of the publication threw daggers: “We think Gwyneth’s cue-ball hairdo was too severe; her dress hung too low. (Get thee to a tailor, quick!)” Cultural critic Camille Paglia was more ruthless in Salon. Noting that Joan Rivers compared Gwyneth to Grace Kelly (quite the compliment!), Paglia snapped, “For the entire evening, big-jawed Paltrow, with her nasal, teeth-clenching Lisa Kudrow style, looks like a Green Bay Packers cheesehead tottering atop a mushy pink Hostess cupcake.” Loved or hated, for something so simple, the dress was surprisingly notorious. A gossip item in the New York Daily News quoted Monica Lewinsky at the Vanity Fair Oscar party, quipping, “Finally, a dress more famous than mine.” All this attention possibly had more to do with Gwyneth’s onstage performance: The Guardian deemed her “worst actress” for what it called a “hammy display of false emotion” during her lengthy acceptance speech. While Gwyneth’s voice cracked as if she was crying, the author could not spot any tears.
Cultural opinion remains split on Gwyneth. Jovial hatred of her has long existed, but it became even more widespread after she founded the luxury lifestyle brand Goop and started shamelessly recommending inordinately expensive items. Over the years, people have come out of the woodwork to diss the 1999 Oscar gown — even as the likes of Vogue name it an all-time favorite. In 2012, Stacy London took a swing: “Her boobs barely even fit in it! It was so stupid, but she won the Oscar, so I guess I’m bitter,” she said in Us Weekly. Even Gwyneth’s own mother told Us in a separate interview, “It didn’t fit her very well.” (Us seems to have specific beef with this dress.) Gwyneth’s dry-eyed speech has remained a sticking point, too. Anne T. Donahue wrote in Paper that “upon winning an Oscar for her turn in Shakespeare in Love, a weeping Gwyneth Paltrow took to the stage in her pink Ralph Lauren dress and ruined sincerity for all.” Ruined sincerity!
Maybe Gwyneth’s tears were fake. Maybe her style was too girlish. But now we know that even as she was up there thanking Harvey Weinstein, she was also covering for him—her sexual harasser—facing the knowledge that if she spoke up, he could ruin her career as quickly as he had help make it. Perhaps there’s a good reason that Gwyneth couldn’t be her authentic self, that she couldn’t shed those real tears critics were looking for. It’s impossible to guess what could have been running through her head that night, but maybe sweetness was the only answer.
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