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

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Size up with these simple, comfortable Sandler-core looks

Written byPaul Julch, MA|Edited byCheyenne Main

Last Updated: September 24, 2023Fact Checked

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  • The Classic Adam Sandler ‘Fit
  • |
  • Adam Sandler Outfit Ideas

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.

Things You Should Know

  • To dress like Adam Sandler, wear basketball shorts, Hawaiian print polos, or other comfy clothing items with tennis shoes, brown moccasins, or Ugg boots.
  • Wear a puffer jacket, a puffy vest, a fleece jacket, or a zip-up hoodie if you want to add an extra layer.
  • To accessorize, throw on a wide-brimmed straw sun hat or baseball cap, wear a fake goatee, or carry around a coffee cup or jar of pickles.

Section 1 of 2:

The Classic Adam Sandler ‘Fit

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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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Section 2 of 2:

Adam Sandler Outfit Ideas

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  1. 1

    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.

  2. 2

    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.
  3. 3

    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.

  4. 4

    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.
  5. 5

    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.
  6. 6

    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.
  7. 7

    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]
  8. 8

    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]

  9. 9

    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.

  10. 10

    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.

  11. 11

    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]

  12. 12

    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.

  13. 13

    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.
  14. 14

    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.

  15. 15

    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.

  16. 16

    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.

  17. 17

    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.

  18. 18

    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.

  19. 19

    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.

  20. 20

    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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      About This Article

      How to Dress Like Adam Sandler: 20 Iconic Outfit Ideas (39)

      Written by:

      Paul Julch, MA

      Personal Wardrobe Stylist & Speaker

      This article was written by Paul Julch, MA and by wikiHow staff writer, Cheyenne Main. Paul Julch is a Personal Wardrobe Stylist, Speaker, and the founder of Urbanite | Suburbanite, a wardrobe styling business in the San Francisco Bay Area. With over 25 years in the fashion industry, Paul works with clients to make getting dressed easier, less time consuming, and more enjoyable. Paul has years of experience in retail visual merchandising - styling windows, displays, and floor sets for Banana Republic, Gap, and Express. He also has experience styling fashion photo shoots and corporate videos. Paul holds a BS Degree in Management from State University of New York at Binghamton, an MA in Clinical Psychology from Long Island University. He also studied Interior Design at the University of California, Berkeley. This article has been viewed 26,373 times.

      9 votes - 100%

      Co-authors: 4

      Updated: September 24, 2023


      Categories: Fashion

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


      What should I wear to dress like Adam Sandler? ›

      Things You Should Know

      To dress like Adam Sandler, wear basketball shorts, Hawaiian print polos, or other comfy clothing items with tennis shoes, brown moccasins, or Ugg boots. Wear a puffer jacket, a puffy vest, a fleece jacket, or a zip-up hoodie if you want to add an extra layer.

      What does Adam Sandler always wear? ›

      The actor often rolls up to on talk shows and red carpets in basketball shorts, baggy cargo shorts, shirts, hoodies, sneakers, Uggs and always white socks. “Parachute basketball shorts are basically Adam Sandler's second skin, every article of clothing needs to be extra large and extra cozy.” @wavykarenk continued.

      How to create the perfect outfit? ›

      Style Defined: How To Build An Outfit In 12 Steps
      1. Jump To: ...
      2. Check the weather. ...
      3. What are you doing that day? ...
      4. What color do you feel like wearing? ...
      5. Pick one item that you want to start with. ...
      6. Have no more than one statement piece. ...
      7. Balance your outfit proportions. ...
      8. What will be your layer or layers for your outfit?

      Does Adam Sandler wear Hawaiian shirts? ›

      Adam Sandler rocked a hilariously eccentric outfit: wine red shorts and a Hawaiian shirt covered in pink and violet feathers. Topped with a zany hat and oversized sunglasses, he embodied his signature comedic style, drawing laughter and turning heads wherever he strolled.

      What shoes does Adam Sandler wear? ›

      I've been rocking Hokas since 2017 (thanks, Dad!), and Cliftons are a great pair of entry-level dad shoes that marry style with function.

      Has Adam Sandler wear Crocs? ›

      #throwbackthursdays Adam Sandler's The Longest Yard premiere didn't stop him from wearing a normal day's outfit. As the actor posed with Nelly, he sported some taupe-colored Crocs at Hollywood's Chinese Theatre. Celebs with Crocs!

      Why does Adam Sandler dress so sloppy? ›

      In an interview with Barstool Sports, Adam Sandler revealed that he started wearing baggy clothing when he was younger because he was "jacked."

      Why does Adam Sandler wear hoodies? ›

      Adam says he choose to wear “whatever's clean in the closet” and often chooses hoodies because “hoodies always feel good… They're comfortable and it covers up some problems.”

      Does Adam Sandler ever wear a suit? ›

      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.

      How can I look cute in every outfit? ›

      If you're trying to look cute, wear cute clothes, like skirts or dresses instead of pants or shorts. Also, choose clothes in pastel colors or with floral patterns, which are super cute. Add a chunky ring or some bangles to complete your cute outfit. When it's time to do your makeup, go for a natural look.

      What makes an outfit attractive? ›

      There are four basic elements that make an outfit interesting; Color, pattern, shine, and texture. Because these elements will add dimension, your look will be anything but boring.

      How can I look cool in every outfit? ›

      How to Look Put Together
      1. WEAR CLOTHES THAT ACTUALLY FIT. In the words of Stacy and Clinton from “What Not to Wear”, “if you don't have fit, you don't have style”. ...
      6. BE CONFIDENT.

      What religion is Adam Sandler? ›

      Sandler with his two daughters, Sunny and Sadie, in February 2011, at a ceremony for receiving a star on the Hollywood Walk of Fame. Sandler has been married to Jacqueline "Jackie" Sandler (née Titone) since 2003. She converted to Sandler's religion, Judaism. The couple have two daughters, Sadie (b.

      Why does Adam Sandler wear a unh shirt in Grown Ups? ›

      Actually the UNH shirt Adam Sandler is wearing in this shot from his 2010 Comedy "Grown Ups," represents the University of New Hamphire Wildcats. Adam did attend Manchester Central High in New Hampshire after moving from Brooklyn for his adolescent years.

      Why does Adam Sandler wear Syracuse shirts? ›

      Big Daddy (Feature film, 1999) - Several mentions; Adam Sandler's character is a Syracuse University alumnus (attended Syracuse University College of Law) and wears various Syracuse sweatshirts and T-shirts.

      Does Adam Sandler wear suits? ›

      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.

      How to dress like a rock star boy? ›

      Little boys can wear pants with faux leather, velvet, or spandex and complete the look with a blazer with vibrant pattens. All rockstars need the right gear to make their statement. Rock fashion features heavy metal accessories, including bracelets, studded bracelets, and necklaces.

      How to dress like a celebrity? ›

      Fashion Risk-Taking: Celebrities are known for taking fashion risks. Whether it's bold patterns, unique accessories, or unconventional pairings, they push the boundaries. Tailoring Matters: The fit of clothing can make or break a celebrity look. Tailoring ensures that their outfits accentuate their best features.

      How to dress like Billy Madison? ›

      Billy Madison's costume is a grey shirt with 'Frank' written inside, a singed knit sweater, green cargo shorts, a yellow cap, and hiking boots.

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