Conan O’Brien. A Wicked medley. A potential Demi Moore sweep. What could go wrong at this year’s Academy Awards?
A lot, apparently.
While most of the A-list attendees and nominees Sunday went for traditional outfits, comfortably rocking a favorable black-tie tuxedo or champagne ballgown, others instead opted to dress in something out of left field—and failed in spectacular fashion.
From the suits that tried too hard to be different, to the gowns that didn’t try enough: Here are the most questionable looks from the 2025 Academy Awards.
Cynthia Erivo
For someone who has consistently delivered throughout Wicked’s press tour and award show circuit, the expectations for Cynthia Erivo were particularly high Sunday night—but—the nominee’s last stop from Oz to the Academy Awards left much to be desired.
Wearing a custom-made Louis Vuitton gown, Erivo kept true to Elphaba and opted for an emerald-green, velvet ensemble accentuated by sharp, geometric cutoffs at the neckline and a ludicrously capacious train.
While Erivo’s dress did hold space for a capital M moment on the carpet, it also paled in comparison to other standouts that she’s worn in the past (like her custom Thom Browne for Wicked’s November premiere in Mexico City) that arguably perfectly balanced camp with couture in ways this dress did not.
Timothée Chalamet
It’s Tweety Chalamet!
While the A Complete Unknown actor is famously allergic to a basic suit and has donned numerous looks over the years that swiftly became meme fodder, his head-to-toe butter-yellow suit for the 2025 Academy Awards missed the mark in the eyes of many critics.
The custom Givenchy getup immediately turned heads Sunday night with a handful of social media users proceeding—yet again—to give Chalamet a meme lashing.
This time? Curious George’s The Man in the Yellow Hat comparisons.
The look also earned Chalamet a roast from the event’s host Conan O’Brien, who applauded the actor for making sure he won’t get hit on his bike tonight.
Elle Fanning
Elle Fanning’s Givenchy gown may have been simple and classy, but it also was painfully boring.
Complemented by a big, black, tragically misplaced bow, Fanning donned a white, floral-embroidered gown that at a quick glance was giving more decorative table sheet than Oscar gown.
Brandi Carlile
Wearing polka dots to perhaps one of the biggest black-tie/high-brow events of the year is certainly a choice, and singer Brandi Carlile seemed to have no fear making it.
The Grammy winner showed up Sunday night wearing a polka-dotted blazer cinched together with a big, red bow, courtesy of Valentino. And despite the pop of color right at the middle, it did not save the look from being drab.
Omar Apollo
Another Valentino look, singer Omar Apollo showed up in a custom ensemble Sunday night which dared to ask: what if Downton Abbey had a Zara store?
Apollo, who made his acting debut in Luca Guadagnino’s Queer last year, donned a polka-dotted shirt, sleek black blazer, patterned scarf, reptilian brooch, and—in case there weren’t enough accessories—a netted headpiece.
While it’s understandable that attendees would want to stray away from traditional suits, there surely must be a line.
Whoopi Goldberg
Why Whoopi, why?
The View host showed up to the red carpet Sunday wearing a Christian Siriano gown. The deep blue ensemble boasted an almost luminescent fabric to evoke the feeling of moving water, and while the physics were admirable, there also was arguably something terribly off with Goldberg’s look.
Some online compared it to a crushed Cybertruck.
Joe Locke
Yet another victim of the Zara sale at Downton Abbey.
Heartstopper’s Joe Locke opted for a Celine ensemble Sunday that appeared to be a standard tailcoat suit and bowtie—but with a gold (bedazzled?) vest? To top it off, the actor for some reason paired all of the above with grey trousers, resulting in an amalgam of pieces that simply did not mesh.
Lisa
It was a rare miss Sunday night for Lisa of K-pop group BLACKPINK.
The rapper, dancer, and newly minted White Lotus star stepped onto the carpet in a Mark Gong floor-length blazer and buttoned shirt that featured a pop of red thanks to a floral pin. Unfortunately though, nothing could not save the getup from looking like an orchestra composer’s couture dream (or nightmare). Remember that one Tom & Jerry episode?
Zoe Saldaña
Zoe Saldaña may have won Best Supporting Actress for Emilia Pérez Sunday night, but her dress was anything but a winner.
The actress sported a look from Saint Laurent which, when exclusively observed from the top half is stunning, but evokes a curtain from the bottom up.
Adam Sandler
The most iconic. The most egregious. And the most memorable look of the night goes to Adam Sandler.
As called out by O’Brien during his opening monologue, Sandler attended Hollywood’s biggest night in his staple hoodie and basketball shorts (it was in fact all part of the bit).
“You’re dressed well, Adam,” O’Brien quipped at one point, singling him out. “What are you wearing?”
“Nobody even thought about what I was wearing ’til you brought it up!” the comedian yelled back.
“You’re dressed like a guy playing video poker at 2 a.m., Adam,” O’Brien then said, prompting Sandler to say: “You know what, Conan?! I like the way I look.”
“I don’t care about what I wear, what I don’t wear! Goodbye, my snazzy gym shorts and fluffy sweatshirt that offend you so much that you had to mock me in front of my peers!”
