The Worst-Dressed Stars At The Oscars 2026

As far as awards show fashion goes, the 98th Academy Awards (that'd be the 2026 Oscars for those who've lost count) didn't have the worst lineup of all time. In fact, if anything, we were pleasantly surprised for the most part. However, there are always some disappointments — and you'd better believe we're going to name and shame. 

Kicking things off: Kylie Jenner. We know, we know, she looked great. Snaps should also go to Schiaparelli for the clever play on the classic keyhole cutout. However, it also came across a little basic, and boring — especially considering Kylie Jenner's most inappropriate outfits. 

Given that her sparkly red dress still showed plenty of skin at an event not typically known for naked dresses et al, that's really saying something. As for the Jessica Rabbit reference on Instagram, we're tired, Kylie. But, having said all that, she definitely wasn't the worst.

Of course, we couldn't dissect Kylie Jenner's lewk without issuing some stern words for her partner, Timothée "hates opera and ballet" Chalamet, as well. The "Marty Supreme" star's all-white Givenchy suit was cool in theory, but in reality it looked messy, and not in a nonchalant way either. While Chalamet has undergone a stunning transformation throughout his time in the spotlight, the Oscar nominee's rugged hair and beard vibe just feels like he's trying way too hard. Chalanting, if you will. 

This one hurt. A lot. But we're nothing if not impartial, and Kristen Wiig's Elie Saab ensemble looked like it came straight outta 2008. A lot of that was down to the styling. Chunky jewelry and a saltwater blowout on top of a deep scoop with wide straps? It's too much. In fairness, the "Bridesmaids" star did joke that she and her former co-stars were "not good with numbers" (via YouTube) while presenting the awards for Best Original Score and Achievement in Sound, so maybe she heard about the 2016 revival and overshot the mark. 

Hear us out, because we know the argument for Emma Stone's custom Louis Vuitton dress will be, "BuT iT's So AnGeLiC." We get it. But even angels can be washed out by the wrong color, and unfortunately for the two-time Oscar winner, that was sadly the case here. Another unfortunate drawback of this particular shade is that in an effort to not look completely washed out, the actor wore way heavier makeup than usual. While there's no question she looked gorgeous, it also emphasized Stone's rumored plastic surgery transformation, and kind of gave us Mar-a-Lago housewife vibes too (eek). 

Gwyneth Paltrow is absolutely stunning, but why she decided the Oscars were the appropriate place to wear a dress with sheer panels all the way up the sides to her armpits is completely beyond us. Evidently, many a social media user felt the same, with several weighing in on the dress being a terrible choice for the glitzy event, and some even going as far as calling it "tacky" on Instagram. Was it Paltrow's sketchiest moment? Not by a long shot. And, to be fair, for another event, we'd be first in line to give her snaps. For the Academy Awards, though, this was not it. 

If Gwyneth Paltrow's side splits were tacky, we're not even sure how to describe Kevin O'Leary's look. A gaudy Dolce & Gabbana jacket (which, he bragged on Instagram, took seven months to create) was one thing. Paired with a Tiffany & Co. framed Triple Logoman (which O'Leary also bragged could have cost as much as $30 million) and Mr. Wonderful looked like he made a bad deal (or lost a bet) with O'Leary's "Shark Tank" co-stars. As one Instagram user quipped, his look "Feels like when you hear an adult say 6-7."

We don't see Barbra Streisand much anymore, so when she appeared at the 2026 Oscars to pay tribute to Robert Redford, with whom Streisand famously had a great relationship, we got teary-eyed fast. Unfortunately, we were let down by her chosen ensemble for the evening, which looked way too casual for the 98th Academy Awards (the shirring on the neckline was a dead giveaway that it wasn't formal enough). That said, it is Babs, so we'll give her a (hesitant) pass.