If there’s a time for best-dressed lists, it’s Oscar night. The Oscars are the red carpet all red carpets wish they could be, the one where the world’s most prestigious actors present themselves in the way they’ll be remembered decades from now. Unlike, say, a wedding — which in Hollywood, who knows how that’ll turn out? — the Academy Awards has a pretty high likelihood of becoming the actual best night of attendees’ lives. And they dress like it.
At this year’s Oscars, stars like Gemma Chan, Angela Bassett, and Linda Cardellini have been praised for their pink, poofy gowns, while Best Actress nominees Glenn Close and Melissa McCarthy have perfected the art of the elegant cape. These, along with other trends, from gender-bending fashion to ’70s glam rock–inspired looks, have dominated the red carpet.
How we determine the “best” looks of the night, though, is a bit more complicated than simply trend-spotting. Best-dressed lists have a long history, but they’re less important than they used to be: As viewership for televised events like the Oscars (and the Super Bowl, for that matter) have declined, so too has the venerable institution of the best-dressed list. Sure, you can still find them pretty easily in newspapers like the LA Times, pop culture stalwarts like People and E!, or fashion websites like the Cut or Fashionista. But do they even matter anymore?
For tonight’s Oscars, we’re including the celebrities on the red carpet who are using their clothes in exciting ways (and whom, yes, people are talking about) while also explaining why they ended up here — and likely every other best-dressed list, too, all broken down into a few main trend categories.
The 2019 Oscars were another red carpet where stars played with gender norms
Once again, this year’s Oscars was a time for celebrities to play with gender fashion norms. Women wearing pantsuits on the red carpet is nothing new, of course, but it felt particularly fresh on Eighth Grade breakout star Elsie Fisher. At just 15, she’s already established herself as an exciting character in fashion, having spent the past half-year on the promotion cycle wearing menswear-inspired sets that still scream, “I’m a teen, and I’m fun!” Stars like Amy Poehler and Awkwafina are also wearing menswear-inspired suits.
Billy Porter, star of the FX series Pose, which centers on the drag ball scene of the 1980s, has also made a name for himself as one of the men leading the way in feminine red-carpet attire. At the Golden Globes, he wore a bedazzled cape lined with hot pink fabric, though his Oscars look was somewhat more demure: a tuxedo gown and what appeared to be a hoop skirt, swathed in velvet.
Many stars went for playful glam vibes for an otherwise relatively boring event
Perhaps inspired by the aesthetic of Best Picture nominee Bohemian Rhapsody, playful looks that nodded to glam rock were all over the red carpet. But there’s another theory here: The Oscars this year are ... kind of a mess. Why not wear something a little bit outrageous?
There was Spike Lee’s tribute to Prince — the director wore a custom diamond necklace with Prince’s symbol, an entirely purple suit, and gold Jordan sneakers that he commissioned himself. “I don’t care what nobody’s wearing,” he told the New York Times in the days before the event. “I win the Oscar on the red carpet. Men, women, I don’t care if they’re wearing 15-inch heels. They can’t be messing with the Jordans I’m going to be wearing. I’m going to be as clean as the board of health. I’m going to be sharp as a razor.”
Presenter and star of Crazy Rich Asians Awkwafina went with a sparkling lilac pantsuit that wouldn’t be out of place on Harry Styles, complete with a pussy bow.
Big, pink, and poofy was a big theme
Speaking of playful, women had no qualms about going full princess for this year’s Oscars. With ensembles like Kacey Musgraves’s and Linda Cardellini’s tulle confections, there’s a bit of irony at play too. Gemma Chan and Angela Bassett, the stars of two of this year’s biggest blockbusters, also showed up in dresses to match. (Bonus: Jason Momoa in a pink velvet suit.)
It’s the year of the elegant cape
Capes, though a longstanding red-carpet trend, went particularly demure this year, with iterations sported by Best Actress nominees Glenn Close and Melissa McCarthy. Capes can do a lot for a look and styled the wrong way can appear costume-y, but these iterations were anything but. We’re also counting Olivia Colman’s emerald train as a cape, because why not.
Big, poofy, and pink ... plus capes
Naturally, the star that combined two of this Oscars’ most fun red-carpet trends was presenter Maya Rudolph. Though fashion critics Tom & Lorenzo called it “tragique” and likened it to a bedding set, Rudolph’s look was every bit as playful as the woman herself.
Young A-listers often don’t stray too far from sparkly dresses at the Oscars
Despite the fact that this year’s Oscars were markedly more fun than usual, young A-listers often tend to stick with what’s worked in the past: a sparkly, form-fitting dress. Emma Stone, Brie Larson, and Amy Adams all went back to the basics. They look great, of course, but that’s kind of their job, particularly at the Oscars.
The evolution of the best-dressed list
Best-dressed lists have a very clear origin story. There was, in fact, a single column that made best-dressed lists a thing in the first place: the International Best-Dressed List, compiled by fashion publicist and founder of the Council of Fashion Designers of America Eleanor Lambert in 1940. Every year, Lambert would create an updated version of the list, until she handed over the reins to Vanity Fair in 2002.
These days, of course, most major newspapers and magazines tout their own iteration of the best-dressed list for all the biggest red carpets. How the stars end up on them is complicated — often, it’s a delicate balance between meeting expectations of what a celebrity might wear and then defying them. (The women of Black Panther during its press tour, for instance, wore mostly dreamy floor-length gowns that still nodded to superhero armor as well as the Afrofuturist aesthetic of the film.) And it’s almost never about the garment alone — at this February’s Grammys, Cardi B wore a vintage Mugler dress that appeared as though she was emerging from an oyster and ended up on nearly every best-dressed list. A cool look, to be sure, but one that not many stars could pull off to quite so much universal acclaim.
The ubiquity of best-dressed lists, however, might be attributing to their decline. Because for nearly the past decade, it isn’t just fashion editors who get to have a say in which stars are the best-dressed of the evening; it’s everyone with a social media account.
”With the democratization of fashion and the rise of social media and blogs, does what people at one fashion magazine say really matter?” Erin Weinger, a fashion editor who has worked at Vogue Australia, the LA Times, and the Hollywood Reporter, told Vox in 2017.
With the decline of newspapers and magazines as institutional leaders in cultural criticism — as well as the death of the kind of televised fashion criticism perfected by Joan Rivers — many more of the relevant conversations about red-carpet fashion are taking place on social media, where people can discuss and dissect outfits in real time rather than wait for a fashion editor to hand down judgment. Plus, by the time many of these best-dressed lists are published later in the evening or the following morning, they’re irrelevant: The court of public opinion has already come to a decision.
How actors and actresses end up on best-dressed lists
In turn, that’s caused many websites to treat best-dressed lists as a regurgitation of what people on the internet are talking about. “If an actress happens to be trending on Google search and there’s nothing otherwise newsworthy to say about her, putting her in a best-dressed list can be a good way to get that clickbait in there,” Weinger added.
That’s why most of the time, best-dressed lists just happen to include the buzziest celebrities in attendance: Outfits only really seem to matter when the person wearing them is worth caring about. (There is a musician whom I will not name, because I do not want to give her the publicity she so desperately craves, who always shows up to events in full-on MAGA gear. She makes sure to arrive very, very early, because she knows that once the real celebrities start to arrive, nobody will include her in their roundups because no one knows who she is.)
It’s part of what makes best-dressed lists so predictable, however. Scroll through any best-dressed list from the past few years and you’ll notice the same names pop up over and over again: Meghan Markle, Cate Blanchett, Lupita Nyong’o, Amal Clooney, Margot Robbie. They’re women who, yes, are conventionally thin and beautiful, but they’re also women whom people already admire. They don’t get caught up in messy Instagram drama or say the wrong thing in interviews. They act and dress elegantly, but never so elegantly that it becomes boring, and they have stylists who are paid lots of money to help them walk that tightrope. Meanwhile, in the mid-2000s heyday of worst-dressed lists, you could expect to see women like Lindsay Lohan or Paris Hilton: big names, sure, but complicated ones.
The “who” of the red carpet is equally important on social media, but there, it operates in multitudes. Even if Rihanna does the most un-Rihanna thing possible and wears something actively uninteresting, there’ll still be a Rihanna stan account ready to defend her choice. Social media users, too, are much more likely to call out actors for missteps like cultural appropriation than an established magazine, which may not want to risk negative coverage about a celebrity it thinks its audience likes.
So if best-dressed lists are really just filtered versions of the conversations already happening on Twitter, and all that really matters is the celebrity, not the dress, what’s the point of best-dressed lists at all? It’s hard to say.
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