Adam Sandler's Best Casual Looks Over the Years: Photos (2024)

The Sandman abides! 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!” 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.”

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“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:

Credit: Christopher Peterson / SplashNews.com

Adam Sandler, King of Unbothered Casual Style: See His Best Looks

The Sandman abides! 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!” 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.[sendtonews type="float" key="FZdTRaVb49-3119873-14453"]“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:

Credit: Christopher Peterson / SplashNews.com

July 2023

Sandler looked as carefree as ever in a flora polo, gym shorts and orange sneakers while walking to lunch at a restaurant in the SoHo neighborhood of New York City.

Credit: Sipa/Shutterstock

June 2007

The Saturday Night Live alum wore slippers to the premiere of Evan Almighty.

Credit: Stewart Cook/Shutterstock

December 2008

Sandler wore a hoodie and jeans on the red carpet.

Credit: Matt Baron/BEI/Shutterstock

July 2009

The Click star upgraded his casual look with a button-down shirt at the world premiere of his movie Funny People.

Credit: Jens Kalaene/EPA/Shutterstock

July 2010

Sandler's slippers made another appearance at the German premiere of Grown Ups.

Credit: John Angelillo/UPI/Shutterstock

September 2012

The Happy Gilmore actor's signature look was a perfect fit for a tennis exhibition in New York City.

Credit: Jim Ruymen/UPI/Shutterstock

June 2019

Sandler chose corduroy pants and a track jacket for the Los Angeles premiere of Murder Mystery.

Credit: MediaPunch/Shutterstock

June 2019

The Waterboy star didn't even bother to tie his shoes for a New York City coffee run.

Credit: Eric Charbonneau/Shutterstock

December 2019

For the premiere of Uncut Gems, Sandler chose a velour zip-up hoodie and his beloved corduroy pants.

Credit: MediaPunch/Shutterstock

January 2020

Sandler fit right in at a charity softball game in Malibu, California.

Credit: Press/Shutterstock

September 2021

The casual style king waved to fans while filming Hustle in Philadelphia.

Credit: Broadimage/Shutterstock

November 2021

The 50 First Dates actor forwent tied shoelaces while running errands.

Credit: John Salangsang/Shutterstock

November 2021

Sandler kept it slouchy when Salma Hayek Pinault received a star on the Hollywood Walk of Fame.

Credit: Image Press Agency/NurPhoto/Shutterstock

June 2022

The Murder Mystery 2 star flashed the peace sign at the Los Angeles premiere of Hustle.

Credit: Erik Pendzich/Shutterstock

March 2023

Sandler bundled up in a neon green puffer jacket, which he paired with soft, slouchy pants.

Credit: MediaPunch/Shutterstock

July 2023

While playing basketball with Timothée Chalamet, Sandler rocked a shirt that read, "Let Me Ask My Wife."

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