Adam Sandler Steals The Show In Hooded Sweatshirt & Basketball Shorts At The Oscars

Mar 04, 2025 by apost team

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On Mar. 2, 2025, Adam Sandler made a memorable appearance at the 97th Academy Awards in Hollywood. Staying true to his signature style, the 58-year-old actor showed up in a hoodie and basketball shorts to the black-tie event. Host Conan O’Brien poked fun at his casual look, with cameras capturing Sandler’s hilarious reaction in the audience!

Sandler has built a lasting legacy as one of Hollywood’s most beloved comedic actors. Rising to fame on “Saturday Night Live” in the early ’90s, he became known for his quirky characters, hilarious musical sketches, and undeniable charm. His transition to film solidified his status as a comedy icon, with classics like 1995’s “Billy Madison,” “Happy Gilmore” in 1996, “The Waterboy” in 1998, and “Big Daddy” in 1999, defining a generation’s sense of humor.

The actor’s fashion choices are almost as iconic as his movies – baggy shorts, oversized hoodies, and dad sneakers. His carefree style has inspired countless internet memes, leading him to be dubbed the “king of casual.” Whether at award shows or on the streets, Sandler proves comfort always wins, and fans love him for it.

At the 2025 Oscars, O’Brien couldn’t resist calling out Sandler’s signature laid-back style, leaving the audience in stitches as Sandler hilariously defended his outfit choice.

O’Brien quipped: “You’re dressed well, Adam.” As the cameras zoomed in, Sandler responded, “Conan, what’s up? My brother, what’s going on, man?” O’Brien then pressed further, asking, “Adam, what are you wearing?” 

Sandler, wearing a $175 bright blue oversized Aviator Nation hoodie and dark blue Adidas basketball shorts with black detailing, shrugged off the question. Instead, he turned it around, asking:

“What are you doing right now?” 

But O’Brien stayed on topic, simply stating:

“I’m asking you what you’re wearing.”

Sandler dramatically reacted, insisting:

“Nobody even thought about what I was wearing until you brought it up.” 

O’Brien playfully added that Sandler looked like “a guy playing video poker at 2 a.m.” Still unfazed, Sandler confidently replied, “I like the way I look because I’m a good person... Did my snazzy gym shorts and fluffy sweatshirt offend you so much that you had to mock me in front of my peers?”

Holding back laughter, O’Brien sincerely said:

“Hey, I’m sorry. Adam, I apologize.”

Sandler then jokingly announced his departure, blaming O’Brien.

“It’s him. He’s the one who caused this!” he exclaimed.

As a final send-off, Sandler extended an invitation to the audience.

“You are all welcome to join me for a game of five-on-five basketball at Veteran Park tonight, midnight,” he said.

Before making his dramatic exit, Sandler made a quick pit stop at Timothée Chalamet’s seat. The Best Actor nominee for “A Complete Unknown“ was met with Sandler’s ongoing bit – dragging out his last name in a ridiculously exaggerated way – before getting an affectionate kiss on the head.

Sandler kicked off this “Chalamet” gag at the 2025 Golden Globes after host Nikki Glaser joked that the “Dune“ actor’s last name “sounds like something Adam Sandler would say.”

Naturally, Sandler, seated in the audience, took that as a challenge. Since then, he’s kept the joke alive, even busting out his signature pronunciation on “Saturday Night Live” while introducing Chalamet as a guest.

apost.com

Adam Sandler’s confidence in his style has made him an icon, proving that being true to yourself is the key to success. What do you think about his fashion choices? Let us know, and then pass this along to all the fans of the comedian you know!