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!” the Friends alum 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.
While imitators spend countless hours trying to create their own haphazard outfits, the comedian’s style motto is actually quite simple. “It’s all comfort and it’s a lot of, ‘Hopefully, this fits,'” Sandler told Esquire. “Anything that feels soft I usually buy.”
The Billy Madison star’s signature look is so pervasive that the clothing brand Old Jewish Men named a style of basketball shorts after him. The “Sandler Shorts” retail for $55, and a description on the company’s website advises buyers to go larger than they normally would. “The bigger the better,” reads the page. “To wear these right, size up at least one size.”
“Wear the shorts around the house, to the court, or to your nephew’s bris,” OJM creative director Bryan Seversky told Vogue in December 2021. “[Sandler] dresses for comfort and is unapologetic about it. And there’s something refreshing and genuine about this attitude.”
Keep scrolling for a look back at some of Sandler’s best casual style moments: