Adam Sandler is beloved for his comedy all over the world, but many of his fans are also fascinated with his sense of style.
The Big Daddy actor is known for dressing casually on nearly every occasion, whether he’s taping a talk show appearance or attending a premiere for one of his movies. His penchant for baggy shorts, T-shirts and sneakers is now so established that his peers find it odd when he does wear a suit. Jennifer Aniston, who supported the Uncut Gems actor in March 2023 when he accepted the Mark Twain Prize for American Humor, was surprised to see him dressed up for the event.
“He wore a suit. He never wears a suit!” she marveled during an interview on The Tonight Show Starring Jimmy Fallon after the ceremony. “It is weird because he kind of looks like he’s just playing dress-up. And he kind of just seems very uncomfortable.”
Sandler has employed a laid-back approach to getting dressed for years, but few people took notice until the 2020 coronavirus pandemic caused many people to embrace sweatpants and hoodies as a daily uniform.
“It took a while. I was working that angle for years,” the Hustle actor joked to Esquire in June 2022 of his newfound status as an aspirational style icon. “For a while I was like, ‘Please accept me and the way I dress.’ And 30 years later, they finally came around.”
The “they” he was referring to not only included his fans but also the fashion press, with Vogue declaring him the “fashion icon of the year” in 2021. That same year, he was the most Googled celebrity style icon, and he topped the list again in 2022.
Keep scrolling for a look back at some of Sandler’s best casual style moments:
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