Vogue once dubbed Adam Sandler a “fashion icon” for his signature style that typically features baggy t-shirts and somehow-baggier basketball shorts. But an upcoming Portland celebration will ...

Adam Sandler arrived at the 2025 Academy Awards dressed in a neon blue sweatshirt and basketball shorts, bringing his signature humor with him. Conan O'Brien, the host, roasted him playfully, ...

Find out the origin below. (L-R) Adam Sandler and Timothée Chalamet in the audience during the 97th Annual Oscars at Dolby Theatre on March 2, 2025 in Hollywood, California.

In Defense of Adam Sandler’s Gymcore Oscars Look By Danielle Zickl Published on March 3, 2025 at 12:15 PM Rich Polk/Penske Media via Getty Images ...

“You’re dressed like a guy playing video poker at 2 a.m.,” O’Brien joked, addressing Sandler, who was dressed in an aqua blue zip-up hoodie paired with a floral button-down shirt underneath.

SNL employed both O'Brien and Sandler. Sandler began writing for the NBC sketch series in 1990 and became a cast member the following year, while O'Brien wrote on the show from 1988 to 1991.

Conan O’Brien Slays Oscars 2025 Monologue, Roasting Karla Sofía Gascón and Adam Sandler’s Gym Shorts By Meghan O'Keefe @ megsokay Published March 2, 2025, 7:41 p.m. ET ...

Adam Sandler cracked up the Oscars crowd during Conan O'Brien's opening monologue, encouraging attendees to join him in a game of basketball after the ceremony and then storming out: 'Chalamet!' ...

Adam Sandler made sure he got the last laugh during Conan O'Brien 's opening monologue at the 2025 Oscars. The actor and unlikely fashion icon, 58, made a surprise appearance at Sunday's ceremony when ...

Adam Sandler made sure he got the last laugh during Conan O'Brien's opening monologue at the 2025 Oscars. The actor and unlikely fashion icon, 58, made a surprise appearance at Sunday's ceremony ...

During the 2025 Oscars ceremony this past weekend, clad in a bright, baby-blue hoodie, basketball shorts and a black-and-white Hawaiian shirt, Adam Sandler, who grew up in Manchester, New ...