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Adam Sandler's fashion sense, or lack of it, gained even more notoriety at the Oscars as host Conan O'Brien mocked his casual look in one of the night's skits. The Uncut Gems star, 58, who routinely opts to keep his attire casual for awards ceremonies, attended the 2025 Oscars wearing a blue hoodie and gym shorts. O'Brien, who was hosting his first Oscars, addressed the audience, telling them that "for such a prestigious night, it is important that everyone is properly dressed." He then pointedly asked Sandler, "What are you wearing?"
Sandler began by playing oblivious before appearing to become increasingly angry as O'Brien ribbed him, saying "you're dressed like a guy playing video poker at 2 a.m." Sandler countered, "I like the way I look. Because I'm a good person; I don't care about what I wear and what I don't wear. Does my snazzy gym shorts and fluffy sweatshirt offend you so much that you had to mock me in front my peers?" The exchange was reminiscent of a staged interaction, with some comparing it to Donald Trump and Volodymyr Zelensky's recent argument at the Oval Office.
Eventually, Sandler stood up to leave, telling the audience they were all welcome to join him in a game of "five on five basketball" later. He also spotted Best Actor nominee Timothée Chalamet, and roared "Chalamet!" before giving the "A Complete Unknown" star a hug. The moment instantly went viral on social media, gathering millions of views on X and YouTube. Sandler's goofy dad attire has made him an unlikely fashion icon and earned him a loyal Gen Z fanbase, with many chronicling their favorite examples of his outfits on TikTok.
Meanwhile, other celebrities made headlines at the 2025 Oscars, including Kylie Jenner and Timothée Chalamet, who made their red carpet debut as a couple. Jenner wore a custom black Miu Miu dress, while Chalamet donned a butter yellow leather Givenchy suit. The pair were joined by Chalamet's sister Pauline Chalamet and mother Nicole Flender. The 2025 Oscars also saw Sean Baker's sex worker dramedy "Anora" take home several awards, including Best Picture and Best Director.
The 2025 Oscars were filled with memorable moments, from Adam Sandler's casual look to Kylie Jenner and Timothée Chalamet's red carpet debut. Some of the notable releases and events from the 2025 awards season include:
- Sean Baker's "Anora" winning several awards at the 2025 Oscars
- Kylie Jenner and Timothée Chalamet making their red carpet debut as a couple
- Adam Sandler's casual look at the 2025 Oscars, which sparked a viral moment with Conan O'Brien
- The 2025 Golden Globes, where Jenner wore a vintage silver chainmail Versace dress
- The Berlinale, where Jenner wore a black sequined Balenciaga pre-fall 2024 dress
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