Last year, Jennifer Aniston famously described a “nice dinner” that she had with Adam Sandler. Talking about it in detail on The Tonight Show, she dissected Adam Sandler’s outfits in one succinct line: “[Sandler] shows up in basketball shorts – satin basketball shorts with white piping, and Nike high-tops and a turquoise velour Izod.”
It’s a quintessential chaos from menswear’s mad king. “He says, ‘Vogue says I look amazing like this,’” Aniston said, referring to the 2021 article that called Sandler a style icon. “So thanks, Vogue.”
Vogue actually wasn’t messing around, either. The menswearverse is very proper. It’s filled with perfectly cut suits and sweaters made from some of the most luxurious materials that you’ll ever see in your entire life. And yes, there’s nothing wrong with that. But it should also be fun! And with his big, baggy tees and bigger, baggier shorts, the Murder Mystery actor has a style that injects some welcome freakiness into Hollywood’s collective wardrobe.
Here’s what you can learn from the best Adam Sandler outfits of all time.
#1: Don’t be afraid of mad shades
Adam Sandler has a mad collection of sunglasses. He’s got Maverick-coded aviators. He’s got bright blue, see-through Wayfarers. He’s got ’90s techno wraparounds. And he’s even got a pair of big tortoiseshell Gucci frames that he wears everywhere.
Basically, if you’re really serious about this whole Sandlercore thing (yes, that’s an actual term), get yourself some big shades.
#2: Get your shirt together
For many dudes, finding the right size of clothing can be tough work. It’s annoying, especially when some brands use their own measurement systems. But Sandler doesn’t have time for all of that. He doesn’t have time to hit the changing rooms. And he definitely doesn’t have time to buy two different sizes to see which one fits best. So what does the Uncut Gems star do? Well, no matter what top he’s getting, he takes his “normal” size, and he just goes one or two sizes bigger.
Whether it’s a Hawaiian shirt or a tee or even a wool coat, Sandler loves oversized. And while this is every tailor’s worst nightmare, slouchy is comfortable and effective.
#3: Keep your shorts long
Thanks to big menswear guys like Donald Glover and Paul Mescal, short shorts are having a moment. But during Tommy Hilfiger‘s New York Fashion Week show last month, extra long, extra wide shorts came out in full force. And it’s a trend that some TikTokers are calling ‘Adam Sandler chic’.
The American actor has long been a fan of shorts that go way over the knee. He usually goes for basketball shorts (like when he’s shooting hoops with Timothée Chalamet in downtown Manhattan). But over the years, he’s also been spotted in massive running shorts, shorts with pinstripes, and even shorts decked out in a shiny gold finish.
#4: Basketball shoes with everything
Speaking of basketball, Sandler loves the sneakers. And while most die-hards would go for grail-y silhouettes like the Air Jordan 1 High OG or the Adidas AE-1, Sandler goes niche.
Sure, Sandler likes his Air Jordans. But he always goes for more affordable options like the Air Jordan 1 Mid or the Jordan Why Not Zer0.5 (a trainer from 2021 that nobody really talks about). When he’s not rocking something from Jumpman though, it’s all about the Puma Rise Nitro or the Hoka Project Clifton. During the People’s Choice Awards earlier this year, the Emmy nominee even pulled up in the Under Armour Curry 11 while wearing a suit (which was a full size too big, of course).
#5: Hit up the Ugg plug
On those rare, off-duty days when he’s not in b-ball sneakers, Sandler opts for an old reliable: his well-loved Ugg boots. And do you really blame the man? If you didn’t already know, Uggs are some of the comfiest things out there. They’re decked out in suede, and they’re completely lined with sheepskin.
In his recent appearance on Complex’s Sneaker Shopping, Pete Davidson even named Sandler as his personal Ugg influencer. “I’m a big Sandler fan,” he says on the show. “I think [he] is like 10 years ahead of everyone on fashion, always. And he wore Uggs a lot in the early 2000s. It’s very powerful. You go grocery shopping, or you go to the movies, or you go out of your house in Uggs? Like, that’s cool, man. I fuck with you.”
#6: Pull your socks up
At the end of last year, a new chaos agent divided millennials and Gen Z-ers: socks, specifically, how they’re worn. Back in November, fitness podcaster Phoebe Parsons uploaded a TikTok explaining that “you can tell the difference between a millennial and a Gen Z just by looking at their feet.” Apparently, millennials like to wear hidden ankle socks, while Gen Z is all about crew socks that are a little longer.
But Sandler? Yeah, he pulls his socks aaall the way up. “I go with a lot of XXL even though I’ve been told I don’t need a XXL,” he says in a 2022 interview with Esquire. “I wear the XXL shirts. I wear the XXL shorts. I pull my socks up goofy, and I wear my sneakers.”
#7: Don’t secure the bag
Earlier this summer, Balenciaga dropped a bunch of grocery bags as part of its summer 2024 line. Bottega Veneta then did the same for its spring 2025 collection. That’s great and all, but Adam Sandler maybe did it first.
There’ve been many instances when the Sandman would rather carry all of his personal possessions in a random plastic bag, than buy an actual backpack or satchel. If said bag is full, he just holds on to his phone, keys, and wallet in the other hand like an absolute madman. While this isn’t something that we’d recommend personally, no one said Sandlercore was gonna be easy.
#8: Stay clashy
Sandler never likes to keep things simple. For the 58-year-old actor, it’s all about big, bold colours and weird patterns. And while most guys would wear all of these things separately, this is Adam Sandler we’re talking about here.
Horizontal stripes and polka dots live in the same universe. Basketball jerseys and floral print shorts go together. Golf polos and Off-White joggers are made for each other. And neon green puffers and maroon chinos? Yeah, for Sandler, that’s a match made in menswear heaven.
#9: Buy a couple of everything
In our guide on dressing in your 20s, one of the main things that you should take away from it is that you should buy as many essentials as you can. For example, if you get Sunspel socks or underwear from Uniqlo and it fits well and feels great, there’s no harm in throwing a few of them in your basket. Because who knows when they might sell out or go out of stock forever? And Sandler agrees.
Back in August of this year, Mystery Fashionist uploaded a video on TikTok that went real viral, real quick. In the interview that’s just over a minute long, he asks the comedian for some style tips, to which he replies, “I think I’ve got a bunch of the same socks. The underwear’s kinda similar too.” If it feels right, then it probably is.
#10: Wear what you want to wear
In the same interview that’s got over two million views (and counting), the TikToker asks, “How do you do this? Do you have a specific style? Because you always wear whatever you want to wear, and you never go based on the rules.” To which Sandler replies, “Whatever’s in the closet, I grab it, I don’t think about it much. Most people make fun of me… but I keep moving.”
And while that way of thinking sounds a little chaotic, it also makes a lot of sense. Life’s too short to worry about all of that. You should be able to wear whatever brands you want. You should be able to wear whatever colours you want. And if people disagree, fuck ’em. Like Adam Sandler, just keep moving.
