Timothée Chalamet to Amy Madigan: Worst-dressed celebrities at the Oscars 2026

The 2026 Academy Awards delivered all the glitz, glamour, and cinematic triumphs we expect from Hollywood’s biggest night. But let's be honest. Half the fun of the Oscars is the red carpet fashion, and this year? Well, let’s just say some of our favourite stars might need to have a serious chat with their stylists. From bizarre accessory choices to tailoring tragedies, the internet is buzzing about the looks that simply didn't work. Here is a look at the celebrities who landed on the dreaded worst-dressed lists this year.

Usually, the Marty Supreme star can do no wrong when it comes to breaking menswear rules. But this year? Total miscalculation. While his partner Kylie Jenner skipped the press line entirely in a red Schiaparelli gown, Chalamet walked solo in a stark white, custom Givenchy suit by Sarah Burton. The 1940s-inspired double-breasted blazer and wide trousers had potential! But then he paired them with clunky white boots that completely swallowed the hem, making him look bizarrely bottom-heavy. Add in a pair of casual sundowner sunglasses that felt way too arrogant for the Oscars, and even a cool little black cross brooch couldn't save this one.

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You wouldn't normally look to the Shark Tank boardroom for red-carpet fashion, and well, there's a reason for that. O'Leary showed up in a blazer that was just way too over-embellished. He actually spent a good chunk of his time on the carpet defending Chalamet’s recent controversial comments about opera and ballet, bragging to reporters that he dropped $1,000 on the betting site Kalshi for the kid to win Best Actor. Maybe he should have invested that money in a different jacket.

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The brilliant mind behind Hamnet (and a previous Best Director winner) is known for her cinematic vision. Her fashion vision this year, however, was highly debated. She went for a wildly over-the-top ensemble that just felt too chaotic. The general consensus from fans online? She really should have left the veil at home.

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This one hurts, because she had such an incredible night! Madigan took home the Best Supporting Actress trophy for Weapons, breaking the record for the longest gap between nominations. She even cracked a great joke on stage: "What's different is I got this little gold guy." We love a legend. But we do not love her dress. The red-carpet look just completely fell flat and lacked the undeniable star power she brought to the stage.

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Chalamet's Marty Supreme co-star actually took a really fun risk. She showed up in a daring, all-black outfit with a deep plunging neckline. Honestly? Her hair and makeup were absolutely flawless. But the outfit featured these attached glove sleeves that completely ruined the silhouette. It was so close to being a great look, but those sleeves dragged it right down onto the worst-dressed list.

(Image Credits: Instagram)

This is a classic case of over-styling. The KPop Demon Hunters singer actually had an incredible foundation: a custom Rahu Mishra mini dress paired with stunning David Webb jewelry. Fans were obsessed with the dress! But for some reason, she decided to cover it up with a massively dramatic, distracting jacket. Sometimes, less really is more.

(Image Credits: Instagram)

Couples fashion is a tricky tightrope to walk. You don't want to look like you're wearing matching prom outfits, but you also need to look like you're going to the same event. Fans were quick to point out that the married couple's outfits had absolutely zero cohesion. It just looked like two entirely different red-carpet vibes awkwardly standing next to each other.

(Image Credits: Instagram)