20 Iconic Adam Sandler Outfits & Costume Ideas for 2025
The knee-length basketball shorts, the baggy shirt that doesn't fully match, the shades, the swagger; that’s the DNA of Adam Sandler outfits in a nutshell. In an industry where looks and style are meticulously curated, Adam Sandler has created a signature look that’s characterized by comfort, confidence and complete disregard for fashion norms.
He may have even inadvertently defined an entire generation of relaxed aesthetics by choosing ease over appearance. His style proves that authenticity never goes out of fashion and confidence is sometimes the ultimate luxury. In short, Sandler has managed to turn dressing down into an art form. And to celebrate his style, we’re sharing some of the most memorable Adam Sandler outfits for inspiration and a few ideas on how to recreate them.
Feature images via Gett Images
Jump to Section
- Iconic Adam Sandler Movie Outfits
- Adam Sandler Outfits For Spirit Week
- DIY Adam Sandler Costume
- Adam Sandler Outfits FAQs
Iconic Adam Sandler Movie Outfits
Adam Sandler is best known for his very sporty, casual and laid-back style. He’ll show up to his own movie premieres — normally glamorous events where people are decked out in high-fashion clothes — in hoodies and jeans, because trying too hard is overrated.
Adam Sandler outfits with sweatpants are a core part of his everyday rotation and he has a soft spot for relaxed hoodies and oversized knits, too. To celebrate his unapologetic comfort-first vibe, here are some of the most iconic Adam Sandler movie outfits that perfectly capture his one-of-a-kind style.
1. Happy Gilmore (1996)
Few Adam Sandler outfits are more recognizable than his Happy Gilmore getup. In the movie, he sports a rotation of rugged, casual looks from the 90s, like a flannel shirt thrown over a faded tee, loose jeans or dark work pants and well-worn sneakers or boots. The most recognizable combo has to be the blue-and-green plaid flannel layered over a red T-shirt, paired with gray pants and brown leather shoes — probably because it's on the original poster. The black-and-yellow Bruins hockey shirt also carries over into the sequel.
2. 50 First Dates (2004)
In 50 First Dates, Sandler’s wardrobe leaned heavily into Hawaiian vibes and island-inspired prints. As Henry Roth, he spends most of the film in short-sleeved, boldly patterned Hawaiian shirts paired with khaki shorts and sneakers or flip-flops. His shirts are often splashed with palm leaves, hibiscus flowers or ocean blues and capture the easy, sun-soaked vibe of Oahu.
Even off-screen, during the film’s press tour, Sandler leaned fully into island mode, trading his usual hoodies for colorful Hawaiian shirts. The look fits perfectly with the film’s tropical setting. Bold prints, open collars and relaxed fits defined this era of Sandler style and continue to serve as timeless Adam Sandler outfits inspo for anyone who values comfort with a hint of vacation flair.
3. Uncut Gems (2019)
In Uncut Gems, Sandler’s wardrobe mirrors that of his character, Howard Ratner, which is loud but slick and put-together. On screen, he rocks a mustard-yellow polo shirt under a sleek black leather jacket, paired with dark dress pants, polished shoes, and plenty of gold jewelry: chain, bracelet, watch, the works.
For the Uncut Gems premiere, Sandler took that energy to the red carpet, wearing a yellow and black polo, gray trousers and a gold-buckled belt. Off-screen, he carried some of that character’s swagger into real life for a while, frequently spotted in leather jackets, jeans and boots. The look was a little sleeker, a little sharper, but still very Sandler.
4. Hustle (2022)
In Hustle, Sandler plays a basketball scout, so it’s no surprise his wardrobe is packed with sporty, relaxed staples; a dream for anyone exploring Adam Sandler outfits with sweatpants.
On screen, he favors zip-up hoodies, oversized tees and breathable athletic pants paired with chunky sneakers. Off-screen, while promoting the film, he showed up in one of his beloved Wailea Golf shirts tucked into flowy Off-White sweatpants and dusty orange Hoka One One sneakers.
5. Bedtime Stories (2008)
Sandler’s Bedtime Stories press look was casual with a touch of polish. On the red carpet, he wore a baby-blue button-up with fine black stripes, layered under a navy zip-up hoodie, light-wash jeans, and black loafers. In the film itself, his outfits leaned toward an even cozier aesthetic of soft sweaters, plaid shirts, and worn-in jeans, making his character relatable and warm.
6. Punch Drunk Love (2002)
This may be really obscure and only for major film buffs, but it's a truly iconic look. Sandler's character, Barry, dons an unforgettable oversized blue suit and tie combo in P.T. Anderson's 2002 romantic drama-dark comedy. It's part David Byrne and away from the usual colorful Sandman chic, but instantly recognizable in one of Sandler's more serious roles, similar to Uncut Gems. It's also great for those who can't grow a beard, as he's clean-shaven in this outfit.
Adam Sandler Outfits For Spirit Week
In 2021, Vogue named Adam Sandler a fashion icon, not for his elegance but for his authenticity. He even inspired Adam Sandler Day, celebrated in schools across the U.S., with people dressing like him for fun.
And if you’re thinking of doing the same for Spirit Week, then you should check out these Adam Sandler outfits for inspo. You can use them to put together your own DIY Adam Sandler outfit for last-minute Halloween costume ideas or Spirit Week or whatever themed event you’re celebrating.
7. The Superman T-Shirt Fit
This is arguably one of Sandler’s most iconic looks and one of the easiest to pull off. Start with a classic blue Superman tee, pair it with red-and-blue basketball shorts (or any color you like) and finish the look with white socks, black sneakers and those ever-present black shades.
8. The Pac-Man T-Shirt Fit
For this retro favorite, combine a light-blue Pac-Man shirt with baggy black blue or white Adidas shorts, red New Balance sneakers and white socks pulled high. Slip on some black sunglasses to seal the deal. If you want to layer up, throw a hoodie on top. This ensemble is ideal inspiration for Adam Sandler outfits for Spirit Week, especially if you’re aiming for a nostalgic, early-2000s vibe.
9. The Classic Puffer Jacket Fit
This one is all about that big jacket energy and goes in the category of funny Halloween outfits inspired by Adam Sandler’s style. To replicate it, grab the puffiest navy blue coat you can find, toss it over a green tee and add blue and black basketball shorts. Complete the look with white crew socks, black Adidas sneakers and, of course, sunglasses. You can even go the extra mile with a fake goatee if you want full character commitment.
The other, more modern style, is the infamous North Face buffer jacket, layered over a pink Hawaiian t-shirt with rust-coloured trousers, and bright blue Hoka running shoes. Here, you can sport the full beard. Another option is to go full-on Little Nicky and pop on a full-length baby blue puffer jacket.
10. The Green Monochrome Fit
Out of all the Adam Sandler outfits featured here, this one is a masterclass in color coordination, Sandler-style. It consists of a white baseball cap, a green T-shirt, oversized green shorts and a pair of dark brown moccasin slippers. It’s one of the few times we’ve seen Adam Sandler actually coordinate his colors and the trick to pulling it off is proportion; the clothes should hang loose without swallowing you whole.
11. The Ugg Boot Fit
Only Adam Sandler could make UGG boots a streetwear statement. You can recreate his classic UGG look with orange-and-blue Nike shorts, a forest-green Columbia fleece and a white floral Hawaiian shirt. Accessorize with a simple silver chain or just keep it casual with messy hair and morning coffee. Of course, you can throw your UGGs on with any combination of basketball shorts and baggy tees because Sandler certainly does.
12. The Pickle-Eating Fit
To copy the viral photo of Sandler strolling with a jar of pickles, layer a gray wool trench coat over an orange sweatshirt, add gray dress pants, gray sneakers and a red striped scarf. You can accessorize with a blue duffle bag and, naturally, your jar of pickles.
13. The Straw Sunhat Plaid Shirt Fit
This look is the ultimate “vacation dad” ensemble. Start with a wide-brimmed straw sunhat, then pair a white and green plaid button-down with Adidas basketball shorts (preferably blue ones with black stripes). Lastly, add white socks and basketball sneakers to complete the look.
For the more obscure look, you can try pull off the vintage SNL "Cajun Man" look with an upturned straw hat, blue, white, and red plaid shirt, red suspenders, and a long-sleeve white top.
14. The LA Lakers Fit
It's been well-documented that Sandler is a huge LA Lakers supporter. Take his love of sportswear, combined with his adoration for the team, and replicate it. Go for a loose Lakers jersey and instead of the usual purple T, wear an oddly matched gray and orange one. Just make sure you find the #34, a retired number in honor of Shaquille O'Neal.
DIY Adam Sandler Costume
Whether he’s walking a red carpet or grabbing coffee, Sandler always dresses like a man with nothing to prove. Any ensemble with basketball shorts, Hawaiian print polos and oversized tees paired with tennis shoes, brown moccasins or even Ugg boots is peak Sandler energy.
If you’re looking for easy Halloween outfits or even Y2K outfit ideas for last-minute costume inspiration, these Adam Sandler outfits perfectly capture the comedian’s anti-fashion confidence.
15. The Classic Sandler Fit
When it comes to Adam Sandler outfits inspo, the classic Sandler look reigns supreme. Think baggy T-shirts, basketball shorts and those ever-present black sunglasses. Think of it as the holy trinity of comfort-core. His go-to formula usually includes an oversized red or blue T-shirt or polo, loose basketball shorts (usually blue, but really any color works) and a sturdy pair of sneakers. To switch it up, you can mix in mismatched sweatshirts and you can’t go wrong with Adam Sandler outfits with sweatpants and basketball shoes. Extra points if you sport the New York Jets (NFL), the Boston Bruins (NHL), and the New York Yankees (MLB).
16. The Tonight Show Fit
When Sandler appeared on The Tonight Show with Drew Barrymore and sang their song "Every 10 Years", he wore what might be the most relaxed outfit ever to grace a late-night stage. To recreate it, you’ll want to start with blue athletic pants, a bright blue crewneck T-shirt and a light gray sweater layered on top. Then, finish it off with light blue Nike basketball shoes , or to be exact, the Nike Sabrina 3 "Blueprint" sneaker.
There are also multiple Late Night appearances in which Sandler cameoed, along with his infamous appearance at the Oscars, in full baby-blue hooded glory, where Conan O'Brien mocked his style.
17. The Baby Blue Pants Fit
One of Sandler’s most effortlessly fun looks, this one is perfect for the summer. Pair a red, blue and white striped polo with pastel-blue athletic pants and orange sneakers, with tortoiseshell aviator sunglasses and a coffee cup if you want to fully channel Sandler’s casual vibe. It’s the kind of outfit that shouldn’t work and yet somehow does.
18. The “You Mad?” Fit
This one is an ode to early 2000s internet humor and starts with a white Troll Face “You Mad?” tee layered with a forest-green Columbia fleece jacket on top. Add white and navy basketball shorts, black sneakers and white socks. Top it off with a green and white baseball cap and, you guessed it, black sunglasses.
19. The Pineapple Polo Fit
This Sandler look is one of the easiest to recreate. Throw on some peach XXL basketball shorts, a white printed polo with colorful pineapples, the ubiquitous white socks and colorful running sneakers. Top it off with a mismatched trucker hat and dishevelled hair. And don't forget your Venti Starbucks cup. With just a few simple pieces, this outfit doubles as a hilarious and recognizable DIY Halloween costume.
20. NYC Basketball Fit
For another classic Adam Sandler streetwear look, take notes from Sandler’s viral pickup game with Timothée Chalamet in New York. Pair white and blue basketball shorts with a gray T-shirt (his said "Let Me Ask My Wife"), white socks and colorful orange, blue, black and white basketball sneakers. For an extra touch, douse yourself in water to make it look like swaet.
Adam Sandler Outfits FAQs
How Do I Dress Like Adam Sandler?
Adam Sandler outfits usually go a little something like this: t-shirts three sizes too big, shorts that come to mid-calf, an unstructured sweatshirt and dirty sneakers. It’s all about visibly loose silhouettes and comfort. So, to dress like Adam Sandler, you’d have to adopt the same laissez-faire attitude towards fashion and style.
You can start off with a Polo T-shirt (make sure it’s oversized), basketball shorts and for footwear, you can either choose basketball shoes or high-top sneakers. And lastly, top it off with some sunglasses to complete the look.
What Is Adam Sandler's Style Called?
Adam Sandler’s style has been characterised as quiet luxury, a term referring to understated elegance that doesn’t rely on logos or trends to make an impression. Sandler’s style has also been referred to as the "schlub look," which is shorthand for a slightly messy dad aesthetic. But really, his style is about ease and a sense of confidence that comes from being genuinely comfortable in your own skin. Every oversized T-shirt and pair of baggy shorts is less a fashion statement and more of a visual declaration that he’s got nothing to prove.
Why Does Adam Sandler Wear Oversized Clothes?
Over the years, fans have wondered why Adam Sandler is so committed to his signature baggy look. When asked about it, Sandler once explained that it started when he was young and in shape; he liked surprising people at the beach when he’d finally take his shirt off. These days, he jokes that he dresses oversized for the opposite reason: to keep everything covered up. It’s a perfectly Sandler mix of self-deprecating humor and nonchalance. Whatever the reason, Adam Sandler dresses for comfort above all.
What Brands Does Adam Sandler Wear?
When it comes to brands, Adam Sandler may not flaunt high-fashion labels, but he does gravitate toward a few familiar names like Nike, Levi’s, Columbia Sportswear and Adidas. Other brands like Under Armour, Ugg, Fender and Off-White appear frequently in his streetwear style as well.
At the 2025 Oscars, a now-viral exchange between Conan O’Brien and Adam Sandler perfectly captured the comedian’s famously casual fashion sense. When Conan playfully called out Sandler’s laid-back outfit, Sandler responded, “Nobody even thought about what I was wearing until you brought it up.” Without missing a beat, Conan quipped that Sandler looked like “a guy playing video poker at 2 a.m.” and that pretty much sums up Adam Sandler’s entire approach.
While his style might be simple, it’s undeniably iconic. He’s almost always wearing shorts, especially mesh shorts, which is what makes him so relatable. He’ll usually pair said baggy shorts with an oversized tee and accessorize with shades and comfy shoes. If you’re looking to replicate his signature style, remember to wear whatever makes you feel good, even if it doesn’t match and prioritize comfort above all else.
Not sure if you want to dress up as Sandler for Halloween or Spirit Week? Classpop! has loads of other outfit ideas!
