when an Oscar gown means so much more

It’s the day of the Oscar nominations, and Esther Zuckerman is buzzed. The New York writer has been flat out all day, but manages to find time for a call to talk about her new book, Beyond The Best Dressed: A Cultural History of the Most Glamorous, Radical and Scandalous Oscar Fashion.

The book, which uses drawings rather than photographs to illustrate each of the featured outfits, looks at 23 Oscar winners from Mary Pickford in 1930 to Jenny Beavan in 2016, and writes about what makes their choice interesting beyond the usual blank glamour of red carpet costume. “If you look at Oscar style in a bubble, you’re missing the bigger picture,” she explains. “Gowns are often so much more than gowns.”

Zuckerman, an entertainment writer at Thrillist, adores the Oscars. “My earliest memory of them was Gwyneth Paltrow’s pink Ralph Lauren dress,” she says, referring to GP’s win in 1999 for Shakespeare in Love when she spent ages on the podium tearfully thanking everyone.

“I remember sketching it at school the next day for my best friend. I would have been about 8. And now I get to cover the awards.”

Typically, she says, coverage of the Oscars red carpet outfits “gets flattened into either beautiful and glamorous, or crazy and ridiculous”.

She is more interested in decoding some of the less obvious choices over the past century, and some of its most iconic – not in terms of flat glamour, but for wider cultural context. “It’s not as if the Oscars celebrate the most daring films released every year,” she reminds us.

“They often uphold old-fashioned ideas of what Hollywood is supposed to look like: white, wealthy and unadventurous.”

Once upon a time, it was the studios who told its female stars what to wear on the red carpet, their style parameters dictated by fearsome and legendary Hollywood stylists like Edith Head. Later, it was media commentators from Louella Parsons to Joan Rivers harshly judging female stars’ style choices.

“Appointed by television networks and glossy magazines, these people don’t reward self-expression,” wrote Haley Mlotek in the New York Times.

“They’re implementing a now entrenched notion of what makes a winning red-carpet dress: a glorified prom dress with a couture tag.”

Two movements, one small, one big, have begun to change this. In 2015, in response to red carpet coverage focusing entirely on the frock rather than the accomplished person inside it, the #AskHerMore campaign pushed for change.

And then the post-Weinstein #MeToo movement accelerated the wider conversation quite radically, a shift permeating even the most hallowed and codified of structures – the red carpet. Which, says Zuckerman, has “seemingly ushered in an age of commentary that is, at least on its surface, less cruelly critical of women and their choices regarding fashion or otherwise. In the age of positivity online, worst dressed lists don’t hold the same cachet as they once did.”

Good riddance to all that nasty, bitchy crap.

Instead, let’s take a look at a few of the outfits featured by Zuckerman, and what makes them stand out.

2021: Chloe Zhao’s white sneakers

  • (Best Director, Nomadland)
Chloe Zhao's famous sneakers
Chloe Zhao’s famous sneakers

“So they were Hermes sneakers, but they were still sneakers,” says Zuckerman. “Clearly visible under her ankle-length dress (also Hermes).” Simple, elegant, immaculate, as was her dress, high-necked, long-sleeved, showing neither limb nor torso. 

Her entire look said, with some dignity, this is about my work, not about me as a decorated creature. She was only the second woman ever to win Best Director (Kathryn Bigelow won in 2010). 

Even Vogue approved: “Chloe Zhao proves the white sneaker is the perfect shoe for any occasion, including the Oscars.” Winner.

2016: Jenny Beavan’s jeans, jacket and boots

  • (Best Costume Design, Mad Max)
Jenny Beavan's casual combo
Jenny Beavan’s casual combo

“As a costume designer, Jenny Beavan knows what clothes mean,” says Zuckerman. Her biker jacket, scarf, jeans and boots were chosen “to honour the spirit of the punk rock dystopian world” of the film whose costumes she created. 

Beavan’s hair was not in an elaborate do, or chic chignon. “As far as I’m concerned, I’m really dressed up,” she said, immediately after accepting her Oscar. “The thing that lots of people were missing is that I was wearing a costume,” she later told an interviewer. 

“An homage to Mad Max. I am a storyteller – I’m not interested in fashion. Other than people like Alexander McQueen. The rest is just so much Cinderella stuff.”

2001: Bjork’s swan dress

  • (Nominee Best Original Song, Dancer in the Dark)
Bjork's infamous 'swan' dress
Bjork’s infamous ‘swan’ dress

Bjork’s swan dress has been on display in New York’s MoMA as art, yet remains emblematic of those horrid worst-dressed lists. This is because Bjork and her friend Marjan Pejokski, who made the dress, subverted the Cinderella stuff completely.

“Bjork was in on the joke,” says Zuckerman. “She was having fun with it.” The performer brought eggs with her, which she ‘laid’ on the red carpet as she walked down it – resulting in what she called “life guards” with walkie-talkies running after her saying ‘Excuse me miss you dropped this!’

2000: Matt Stone’s pink dress

  • (Nominee Best Original Song, South Park movie)
That pink dress, on Gwyneth Paltrow and Matt Stone
That pink dress, on Gwyneth Paltrow and Matt Stone

The year before, Gwyneth P had worn that classic pale pink Ralph Lauren (causing Monica Lewinsky to quip at the Vanity Fair after party, “Finally, a dress more famous than mine”). 

Matt Stone decided to wear the same dress the next year – long before the whole gender fluidity thing had gone mainstream.

Instead Stone and his South Park co-creator Trey Parker “wielded their male privilege”, says Zuckerman, by arriving dressed as GP and J-Lo (Parker in a replica of J-Lo’s green Grammys dress). 

It was anarchic and funny, especially as they had both taken acid beforehand and were tripping as they walked down the carpet. providing a surreal visual gag. 

“It took a lot of energy to be that rebellious,” said Stone afterward. You’d wonder though, would two red carpet women have gotten away with such a stunt? The short answer is no.

2010: Gabourey Sidibe’s plus-size body

  • (Nominee Best Actress, Precious)
Gabourey's Sidibe's Grecian red-carpet dress
Gabourey’s Sidibe’s Grecian red-carpet dress

The outstanding aspect of Sidibe’s appearance on the red carpet was nothing to do with her dress – a classic floor-length Grecian-look design – but the fact that she was on the red carpet at all. 

She was not treated the same as other emerging new actresses, either by the industry or its surrounding media, but subjected, says Zuckerman, to “unfortunate hand wringing by the press”. 

Stylists and designers backed away. Eventually, Lionsgate appointed her a stylist, to whom Sidibe said, “I don’t want a dress that will stand out. I’ll do that anyway. I just want to look like I belong.” 

She did in the end. Teen Vogue wrote how she was “a red carpet queen”.

Yet Sidibe’s presence served to highlight just how limited and restrictive our beauty aesthetic really is. Slim and light-skinned, or stay away.

HONOURABLE MENTIONS

  • 1988 Cher’s net ensemble
  • 1974 Tatum O’Neal’s tuxedo
  • 1972 Jane Fonda’s austere black suit
  • 1969 Barabara Striesand’s transparent cocktail pyjamas
  • 1958 Miyoshi Umeki’s kimono
  • 1940 Hattie McDaniel’s gardenias

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