How to Dress Like Adam Sandler: 20 Iconic Outfit Ideas (2024)

Written byPaul Julch, MA|Edited byCheyenne Main

Last Updated: September 24, 2023Fact Checked

We all know that Adam Sandler is a super relatable fashion icon. Whether you’re dressing for your school’s spirit day, you’d like to find a unique Halloween costume, or you just want to achieve Adam Sandler’s comfy laid-back look, we’ve got you covered. Just throw on an oversized t-shirt or polo with a pair of baggy basketball shorts and sneakers. You can always substitute the t-shirt for a jersey (especially a Yankees jersey) and add a zip-up hoodie if it’s cold out. Keep reading for more fashion tips and a list of the best Sandler 'fits!

This article is based on an interview with our personal wardrobe stylist ands peaker, Paul Julch, MA, founder of Urbanite | Suburbanite. Check out the full interview here.

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1. Wear a baggy T-shirt, basketball shorts, and black sunglasses. The signature Sandler 'fit typically involves an oversized red or blue T-shirt or polo shirt, a pair of baggy basketball shorts (any color, but they’re mostly blue), and basketball sneakers. Don’t forget to add a pair of black sunglasses!^[1]

   • Try mixing and matching different colored sweatshirts and sweatpants with basketball shoes to achieve another classic Sandler look.
   • Dressing like Adam Sandler is super easy because he wears whatever makes him feel comfortable—have fun and experiment with items you already have in your closet!^[2]

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   The Superman T-Shirt 'Fit This is one of Adam Sandler’s best-known outfits, and it’s really simple to replicate. Just wear a classic blue Superman logo T-shirt, red and blue baggy basketball shorts, white socks, and black sneakers. Add a pair of black sunglasses and hold a coffee cup to complete the look.

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   See Also

   Best Adam Sandler Spirit Day IdeasWhy high schoolers across the US are dressing up for ‘Adam Sandler Day’

   The Pac-Man T-Shirt 'Fit This look is also easy to copy using items you probably already have in your closet. Try wearing blue, black, and white baggy Adidas basketball shorts, a pair of black sunglasses, a light blue Pac-Man T-shirt, red New Balance sneakers and white socks pulled all the way up.^[3]

   • Add layers if you’d like—you can always slip a hoodie on top to create a more casual, sporty look.
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   The Tonight Show 'Fit Sandler once wore this outfit on The Tonight Show, and people have been talking about it ever since. To replicate it, wear 3-striped blue athletic pants, a bright blue crewneck T-shirt, a light gray crewneck sweater, and black Nike basketball shoes with red soles.

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   The Classic Puffer Jacket 'Fit If you have a truly enormous navy blue puffer jacket you’ve been dying to wear, this outfit is perfect. Throw it on over a green T-shirt with a pair of blue and black basketball shorts, black sunglasses, white crew socks, and black Adidas Gamecourt 2 tennis shoes.

   • Add a fake goatee if you really want to go all-out.
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   Green Monochrome 'Fit For this throwback outfit, wear a white baseball cap (his has the words “Grown Ups” on it, but yours doesn’t have to), a green T-shirt, oversized green shorts, and a pair of comfortable dark brown moccasin slippers.

   • When wearing oversized clothing, make sure the shoulder seams of your shirts are as close as possible to the high point of your shoulder to make sure it doesn’t look like you’re wearing someone else’s clothes.
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   The Yellow Polo 'Fit To recreate this stylish look from the Uncut Gems Red Carpet event, wear a yellow and black polo shirt, gray dress pants, rimless reading glasses, a black leather belt with a gold bucket, a gold chain link necklace, a gold or yellow bracelet, a gold watch, and black loafers with a gold buckle.^[4]

   • If your ears are pierced, pop in a couple of white stud earrings to complete the look.
   • When finding the right belt, choose a size that’s slightly bigger than your waist size.
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   The Ugg Boot 'Fit Adam Sandler proves that Ugg boots go with everything—for this outfit, try wearing them with a pair of orange and blue Nike shorts, a forest green Columbia fleece jacket, and a white floral Hawaiian print shirt. If you’d like to accessorize, try adding a simple silver chain necklace.

   • You can also throw on a pair of Ugg boots with whatever oversized basketball shorts and baggy colorful T-shirts you’d like—Adam Sandler wears them with almost anything.^[5]
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   The Pickle-Eating 'Fit If you’re looking to recreate the viral photo of Sandler walking down the street eating from a jar of pickles, this one’s for you. Simply slip on an orange sweatshirt, a gray wool trench coat, gray dress pants, and gray sneakers. Then add a red striped scarf, and carry around a blue duffle bag and your favorite jar of pickles.^[6]

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   The Straw Sunhat Plaid Shirt 'Fit A big straw sunhat is a Sandler staple, and this outfit is no different. Wear your favorite wide-brimmed straw sunhat, a white and green plaid button-up shirt, blue and black Adidas basketball shorts, a pair of white socks, and basketball sneakers.

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    The Jersey and Sweatband 'Fit For this classic Adam Sandler outfit, try sporting a blue sweatband, a jersey, and a pair of grey and red baggy Adidas shorts. Add a pair of black Nike basketball shoes with red soles and some basic white socks.

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    The Baby Blue Pants 'Fit Try out this fun Sandler look—wear a red, blue, and white striped polo with baby blue athletic pants and orange sneakers. Add a pair of brown tortoiseshell aviator sunglasses and carry around a coffee cup to perfectly match this summer-style inspo.^[7]

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    The “You Mad?” 'Fit Bring back the early 2000s for this ensemble. Dust off that white Troll Face “You Mad?” T-shirt and throw it on along with a forest green Colombia fleece jacket, a pair of white and navy blue basketball shorts, black sneakers, and white socks. Top it all off with a green and white baseball cap and a pair of those iconic black sunglasses.

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    The Happy Gilmore 'Fit If Happy Gilmore is your favorite Adam Sandler movie, replicate one of the costumes by wearing a plaid flannel (black, orange, and blue are some of the patterns he wears), a red or orange T-shirt, a pair of dark gray pants, and a pair of brown leather sneakers or hiking boots.

    • Alternatively, wear a yellow and black jersey with a pair of gray pants to mimic another incredible Happy Gilmore outfit.
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    Neon Green Puffer Jacket 'Fit This is the winter jacket inspo you’ve been waiting for. Take a neon green puffer jacket and throw it on top of a colorful pink and blue floral Hawaiian print polo. Add a pair of brown corduroy pants, some bright blue basketball shoes, and a thin silver chain necklace. If you have some brown-tinted aviator sunglasses, put those on too.

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    White Drink Polo 'Fit For this post-COVID look, wear a pair of gray dress shorts with a white printed polo shirt (his is from Wailea Golf Club and has little drinks printed all over it), a pair of white socks, and white untied Nike shoes. Complete the look by carrying around a basic blue medical facemask.

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    L.A. Family 'Fit Another classic Sandler look from a day out with his family in L.A. To copy the outfit, wear a gray T-shirt (his has surfboards printed across it), baggy white and red basketball shorts, black sneakers, and white socks.

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    NYC Basketball 'Fit Try copying this look that Sandler wore while playing pick-up basketball with Timothée Chalamet in NYC. Throw on a pair of white and blue basketball shorts, a gray T-shirt (his says “Let Me Ask My Wife” on it), white socks, and a pair of colorful orange, blue, black, and white sneakers. Carry around a basketball to really seal the deal.

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    The Bedtime Stories Red Carpet 'Fit For this throwback red carpet look, Sandler went casual and comfy as always. Wear a baby blue button-up with thin black stripes, a navy blue zip-up hoodie, a pair of light blue scuffed-up jeans, and a pair of black loafers.

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    Ugg Boots 'Fit (2021 Edition) If you want more Ugg boot inspiration, you’re in luck! For this post-COVID Ugg updated look, wear a pastel green T-shirt under an orange sweatshirt, blue and white boxers peeking from the top of gold baggy Under Armor basketball shorts, and a blue and gray camo-print face mask with that pair of Ugg boots.

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    The Late Show Throwback ‘Fit If you’re looking for another throwback Late Show outfit, try this one from 2008: wear a gold flat cap hat with a blue and gray padded vest, a red jersey or T-shirt, medium-wash blue jeans, and a pair of brown loafers.

    • Two-color jackets make a great statement piece for any outfit. If you want to look like Adam Sandler, combining lots of statement pieces together can be a great way to go!

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