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 does Adam Sandler say about his clothes? ›

In an interview with Barstool Sports, Adam Sandler revealed that he started wearing baggy clothing when he was younger because he was "jacked." "This is not a lie... I was jacked," Sandler said in the interview below.

What does it mean to dress like Adam Sandler? ›

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.

What is a famous line from Adam Sandler? ›

Chemistry can be a good and bad thing. Chemistry is good when you make love with it. Chemistry is bad when you make crack with it.

What did Adam Sandler wear in Grown Ups? ›

In Grown Ups, actor Adam Sandler can be seen wearing either a different shirt or hat representing a different university in almost every scene. You can see him wearing a UCONN hat, Harvard t-shirt, University of New Hampshire t-shirt, and a University of Rhode Island t-shirt.

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.

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.

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.

What shoes does Adam Sandler wear? ›

Sandler's footwear philosophy is built on comfort as we normally find him in cozy sneakers. From Hoka to Under Armour, the actor prioritizes how the shoes feel on his feet. Jackie Sandler and Adam Sandler at the 2024 People's Choice Awards.

What was Adam Sandler's funny line? ›

"Knibb High football rules!" "YOU'RE GOING TO DIE, CLOWN!" "I bet you know what it's like to get all riled up, Johnny Mac." "…and I don't even like you."

Is Adam Sandler a billionaire? ›

Based on the most recent data available, Adam Sandler's estimated net worth is $440 million, primarily due to his lucrative career in comedy, acting, and film production.

Who helped Adam Sandler get famous? ›

While working at a comedy club in L.A., he was "discovered" by Dennis Miller, who recommended him to Saturday Night Live (1975) producer Lorne Michaels and told him that Sandler had a big talent. This led to his being cast in the show in 1990, which he also wrote for in addition to performing.

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.

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.

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 was Adam Sandler like as a kid? ›

Sandler was raised in Manchester, New Hampshire, the youngest of four children. Academically disinclined, he was frequently disciplined for his comedic antics in school. He first performed at a stand-up comedy club in Boston at age 17 at the urging of his brother.

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