Only Adam Sandler can show up to a fancy premiere wearing basketball shorts and ugly sneakers and somehow be the coolest person there. Seriously. Not only is he a comedy genius, but he’s also a style icon of sorts who could not be bothered to suit up to save his life — and still earns props for it. “It’s all comfort and it’s a lot of ‘Hopefully, this fits,'” Sandler told Esquire when asked about his unique take on fashion. And, really, who needs a tailor when you’re literally Adam Sandler, and dressing like a lazy dad is part of your appeal? “I go with a lot of XXL even though I’ve been told I don’t need a XXL,” he shared. “I wear the XXL shirts. I wear the XXL shorts. I pull my socks up goofy and I wear my sneakers.” Never mind the fact that his net worth is higher than you think — that’s just Adam being Adam.
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But, as with everything else, there comes a point where it all starts to feel tiring. Host Conan O’Brien said it best when Sandler pulled up to the 2025 Oscars dressed in his usual ‘fit of a collared shirt, blue hoodie, and basketball shorts: “You’re dressed like a guy playing video poker at 2 a.m., Adam!” We get that it’s a bit, but our point stands. As for Sandler? He’d like his haters to know that he DGAF. (As much as he’s loved by fans, there are celebrities who clearly can’t stand his sense of fashion and humor). “You know what, Conan? I like the way I look because I’m a good person. I don’t care what I wear or what I don’t wear!” he snapped. However, to be fair, he’s made that last part clear since day one.
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He woke up like this
In 2007, Adam Sandler showed up at the world premiere of “Evan Almighty,” starring his friend and actor Steve Carell, at the Universal CityWalk Hollywood in Los Angeles. Dressed in his signature outfit — a T-shirt, oversized basketball shorts, and fuzzy slippers — he looked as though he’d just rolled out of bed and decided to swing by on his way to the deli. He completed his laidback look with sunglasses and car keys in hand because, well, he’s Adam Sandler, and he’s just too cool to care. At one point, he was joined by his friend Kevin James on the red (or, more accurately, green) carpet, who matched his energy in a printed tee, sunglasses, and hat. But even James made more of an effort by opting for jeans instead of shorts and wearing sneakers over slippers, unlike his “Grown Ups” co-star. Honestly — grow up, Adam.
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He likes to mix and match (but not in a way that makes sense)
By 2016, Adam Sandler still didn’t care enough about the rules of fashion to consider hiring a stylist. Seen here at the red carpet premiere of his Netflix film “The Do-Over,” co-starring David Spade, he sported a green polo shirt and brown corduroy pants that looked at least two sizes too big. He styled them with a blue puffer jacket (ever heard of a suit?), a cheap-looking belt, and brown leather shoes. Talk about a mismatch. But at least he didn’t show up in basketball shorts and sneakers, so — hey, a win is a win. And yet, no matter how inappropriate the look seemed on the red carpet, fans still ate it up. “I love how Adam Sandler gives zero f***s about how he looks on a red carpet,” one Reddit user said. Another chimed in to add: “Hey, he tucked his shirt in, so clearly he gives at least one f***.” Ha.
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Sandler looks lost at Salma Hayek’s Hollywood Walk of Fame ceremony
In 2021, Adam Sandler came out to support his “Grown Ups” co-star Salma Hayek as she received her star on Los Angeles’ Hollywood Walk of Fame. In true Adam Sandler style, he didn’t bother with a suit and instead opted for a more casual look — perhaps too casual. He wore a printed shirt with an oversized maroon jacket, black sneakers, and — get this — track pants. During his tribute speech to Hayek, the actor acknowledged his fashion faux pas, saying, “First of all, Salma, I apologize for not dressing more elegantly. But as you know, Friday is laundry day in the Sandler household. Plus, I just found out I’m deadly allergic to collared shirts and thin black socks.” (Honestly, at this point, it might as well be true.)
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After joking that Hayek’s husband had turned him down when he asked to borrow an extra suit, Sandler added, “I headed over to the nearest Bottega Veneta store in pursuit of purchasing some stylish accessories with my own wallet. I saw the price tags and ran out. Thank you.” Well, it’s a good thing he’s got a good sense of humor!
Either he’s dressed like a hobo or a basketball fanatic
We get that you’d rather be sitting courtside watching hoops being tossed around the court than show up on the red carpet, but Adam, you gotta keep things profesh. During the Los Angeles premiere of Netflix’s “Murder Mystery 2,” starring himself and Jennifer Aniston, the actor stepped out in a classic Adam Sandler ‘fit consisting of a New York Knicks hoodie, beige track pants, and colorful sneakers. He looked way too casual and underdressed while posing next to Aniston, who was in full glam mode in a see-through dress and black stilettos. Even his wife, Jackie Sandler, made an effort to dress up in a stunning cocktail dress with sheer tights, pumps, and a blazer.
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Appearing on “The Tonight Show Starring Jimmy Fallon,” Aniston shared her thoughts on Adam’s signature style. “He never wears a suit,” she confirmed. “[When he does], it is weird because it looks like he’s just playing dress up, and he kind of just seems very uncomfortable.” Recalling a fancy dinner she once had with the Sandlers in Italy, the “Friends” alum said, “Jackie [looked] beautiful, and I looked dressed, and [Adam] shows up in satin basketball shorts with white piping and Nike high tops and a turquoise velour Izod that had no relationship to the black,” much to Fallon and the audience’s amusement. “And it was just…” absurd. There, we finished the sentence for you, Jen.
Sandler’s ‘fit often leaves us scratching our heads
When he’s not dressing up like he’s on his way to grab brunch or watch a basketball game, Adam Sandler is still busy ignoring all fashion rules. Seen here posing with his wife at the 2024 premiere of his Netflix special “Adam Sandler: Love You,” the actor rocked an oversized yellow shirt with red track pants and Jordan sneakers in gold, white, and blue. He couldn’t be more mismatched with his beautiful date, who showed up in a little black dress and mesh kitten heels. Stunning! Not you, though, Adam. This style blunder came just one month after the “50 First Dates” actor pulled up to the 2024 Nickelodeon Kids’ Choice Awards with Jackie and their two daughters, Sadie and Sunny Sandler, in tow. He likewise seemed not to have gotten the memo based on his outfit while accepting the award for best male voice for the animated film “Leo.” He paired a collared shirt with below-the-knee striped shorts, a brown hat, high socks, and Jordan shoes. Don’t ask us, as we’re also very confused.
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