The 15 Most Iconic and Outrageous Adam Sandler Outfits (2024)

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An ode to an unorthodox style icon

The 15 Most Iconic and Outrageous Adam Sandler Outfits (1)

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The 15 Most Iconic and Outrageous Adam Sandler Outfits (2)

By: Jael Rucker

Published Apr 24, 2023

Adam Sandler he's the man if he can't do it no one can. Seriously, if the drip isn't Adam Sandler approved or worn, then it doesn't count on the cool spectrum. Sure Adam Sandler is one of the highest-grossing Hollywood superstars of all-time, sitting pretty at over $2 billion worldwide at the box office. Sure he's had a bunch of memorable roles such as his stint on Saturday Night Live in the 1990s, Billy Madison in 1995, Happy Gilmore in 1996, and 50 First Dates in 2004, but there's a component of Adam Sandler's career that isn't nearly appreciated enough—his awesome and ever-so-slightly goofy style, which we'll be taking a closer look at. Adam Sandler outfits are, quite simply, unique.

Whether you aspire to dress like Sandler, or just simply want to revisit a few of the looks that has helped make him an unexpected style icon, we're doing a breakdown of the most iconic and silly Adam Sandler outfits. Let's get into it.

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1. The Classic Adam Sandler Look

The 15 Most Iconic and Outrageous Adam Sandler Outfits (3)

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If Adam Sandler steps out to run casual errands five times in one week, it's possible that he will be wearing some variation of basketball shorts, a logo tee, and whatever sneakers he feels like rocking on that particular day. This is Sandler's go-to look that he never goes too long without wearing, and who can blame him? It's an automatic in terms of nice drip.

2. Puffer Jacket Sandler

The 15 Most Iconic and Outrageous Adam Sandler Outfits (4)

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But sometimes Sandler will switch it up a bit and hit us with the unexpected, like on this particular day when he stepped out wearing a neon green puffer coat, which he paired with what appears to be a Hawaiian shirt, reddish brown khakis, and blue sneakers.

3. Preppy Sandler

The 15 Most Iconic and Outrageous Adam Sandler Outfits (5)

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If you want an example of an easy-to-duplicate preppy Adam Sandler outfit, then you can check out what he wore to his hand and footprint ceremony at the Mann Chinese Theater in 2005. Jay-Z may have made the Yankees Cap, but Sandler is definitely an honorary member of the Yankees New Era committee as well.

4. Saturday Night Live Sandler

The 15 Most Iconic and Outrageous Adam Sandler Outfits (6)

NBC

Sandler's 1990's Saturday Night Live drip doesn't get appreciated nearly as much as what it should, and neither does his guitar playing and singing skills for that matter either.

5. Uncut Gems Sandler

The 15 Most Iconic and Outrageous Adam Sandler Outfits (7)

Netflix, A24

Is it safe to say that Adam Sander's character in Uncut Gems is his most stylish character ever? Cause we're saying it. Those tinted shades were ultra cool.

6. Uggs Sandler

The 15 Most Iconic and Outrageous Adam Sandler Outfits (8)

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One thing about Mr. Adam Sandler—he's going to wear some Uggs, and most of the time the Uggs will be paired with basketball shorts. How he came up with this exact combination is still a mystery, but it works... for Adam Sandler and Adam Sandler only.

7. Hoodie Sandler

The 15 Most Iconic and Outrageous Adam Sandler Outfits (9)

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Hoodie Sandler is always a vibe.

Sidenote: Does anybody know how many pairs of sneakers Adam Sandler owns? It has to be well into the hundreds (or even thousands) at this point because we've never seen him repeat.

8. Camo Jacket Sandler

The 15 Most Iconic and Outrageous Adam Sandler Outfits (10)

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You know what? Sandler doesn't get enough credit for his jacket game. He's rocked some nice jackets over the decades, including this camouflage one he wore at the 2018 premiere of his Neflix film The Week Of alongside his wife Jackie.

9. Suited and Booted Sandler

The 15 Most Iconic and Outrageous Adam Sandler Outfits (11)

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As per our calculations, Adam Sandler wears a suit approximately once a year. That's it (and sometimes he'll skip a year or two). This occasion doesn't happen often, but when Sandler does turn up in a suit, he does it well.

10. Superman Sandler

The 15 Most Iconic and Outrageous Adam Sandler Outfits (12)

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Cue the music. This outfit still hasn't been topped with the blue Superman logo shirt, red basketball shorts, and the Air Jordans. We'll call this look Superman with a street edge.

11. Blazer Sandler

The 15 Most Iconic and Outrageous Adam Sandler Outfits (13)

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Blazers over simple tees is a look that will never go out of style, and Sandler gave us a masterclass in how to pull it off at the 2010 Grammys.

12. Casual Red Carpet Sandler

The 15 Most Iconic and Outrageous Adam Sandler Outfits (14)

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One of the actors in this picture is dressed visibly different from the others. Can you guess who?

13. Insane Logo Hat Sandler

The 15 Most Iconic and Outrageous Adam Sandler Outfits (15)

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Adam Sandler (who is not nor has ever been a part of the NYPD) pulled up to the 1995 MTV Rock the Vote wearing an NYPD ball cap which is just... insane (in a good way of course). Very 90s.

14. Grunge Sandler

The 15 Most Iconic and Outrageous Adam Sandler Outfits (16)

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In the midst of his five year Saturday Night Live run, Sandler would sometimes channel his inner Kurt Cobain, which was always fun.

15. Plaid Sandler

The 15 Most Iconic and Outrageous Adam Sandler Outfits (17)

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Ahh. The good old days of classic MTV. Also, gotta shoutout the plaid fit from Sandler. A plaid shirt paired with a ball cap is actually a fire combo.

Alright, so now that we've covered Adam Sandler's best outfits to date the wheels are turning in your head as to how you can recreate them right? Here's a few suggestions:

Shop the Adam Sandler Look

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FAQs

What is Adam Sandler's style called? ›

TikToker @wavykaren described Adam Sandler's look as “the ultimate La-Z-Boy style.” Whether you've spotted the comedian at one of his shows, eyed him in the pages of a magazine, or you're going based on his movie appearances, you've likely seen Sandler wear any combination of oversized clothing.

Who is Adam Sandler real wife? ›

For three decades, Adam Sandler has made a name for himself in the entertainment world, but aside from acting, performing and singing, the "Big Daddy" star is also a devoted family man. The funnyman and his wife Jackie Sandler are parents of two daughters.

How much is Adam Sandler's net worth? ›

Sandler had an estimated net worth of $420 million in 2020, and signed a new four-movie deal with Netflix worth over $250 million. Sandler's comedic roles include Billy Madison (1995), Happy Gilmore (1996), The Waterboy (1998), The Wedding Singer (1998), Big Daddy (1999), Mr.

What did Adam Sandler wear in Grown Ups? ›

According to the film's publicist, Sandler decided to wear T-shirts and hats with New England connections throughout the shoot. So viewers will also see gear from Boston University, Harvard, Vermont, New Hampshire and Rhode Island. UConn and Whalers fans can see Sandler's latest when it opens June 25.

What to wear to dress like Adam Sandler? ›

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!

Do Adam Sandler's daughters act? ›

Do Adam Sandler's children act? ›

Does Adam Sandler always cast his wife? ›

Adam Sandler frequently casts his wife, Jackie, and their daughters, Sadie and Sunny, in his movies, showcasing his family in his work. Sandler's film production company, Happy Madison Productions, has been successful in producing hit comedies since its debut in 1999.

What is Adam Sandler's biggest movie? ›

Hotel Transylvania 3: Summer Vacation is the highest grossing Adam Sandler movie to date, with a $528 million box office.

Why does Adam Sandler carry a cane? ›

Adam Sandler has been spotted walking the streets of Los Angeles, California, specifically in Pacific Palisades, accompanied by his wife, the actor used a cane to support himself to walk after undergoing hip surgery.

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.

Why did Adam Sandler get his hip replaced? ›

He explained that he “had been doing so many movies in a row,” including the upcoming film “Spaceman,” in which he was put into a hanging harness for scenes. That's when he noticed his hip hitch. “I kept saying, 'Something's going on with my hip, man. I'm in trouble,'” he recalled.

What is Schlub style? ›

There is no formula for the Schlub look. They do not seem remotely burdened by notions of getting it right or wrong. Their clothing is random and contingent. They are fashion nihilists.

What was Adam Sandler's first feature film called? ›

Adam Sandler made his film debut in 1989, playing an aspiring comedian who takes a gig aboard a cruise ship filled with beauty queens in the little-seen Going Overboard.

What are Adam Sandler's traits? ›

This is evident in his outgoing and playful demeanor, his creativity and spontaneity in comedy, and his ability to connect with emotions and express himself through acting and music. As an Extravert, Sandler enjoys being around others and can easily engage in social situations.

Has Adam Sandler ever wear a suit? ›

(And a bevy of gorgeous fictional mansions.) What he does not have is a tailor, apparently. Sandler generally shuns formal wear, but on some occasions manages to don a suit or even a tux — though he always looks pretty uncomfortable.

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