16 Adam Sandler ICONIC Outfits (With Pictures) - Style and Run (2024)

When it comes to fashion, Adam Sandler is in a league of his own. In fact, he tops the list in Google’s “celebrity outfits” search category over the years consistently.

He’s never ashamed of being himself, and as style expert Robert Verdi said it best, “He looks like he’s on his way to rehab, but people love it because it’s authentic.”

Some would say he’s the embodiment of the Y2K aesthetic.

Sandler always looks comfortable in basketball shorts and baggy tees (it’s his staple look), but he can sport another once in a while. Let’s see some of Adam Sander’s most iconic outfits.

1. The Classic Sandler

The classic Sandler look, also known as “coffee run” Sandler, consists of oversized basketball shorts, a tee shirt, and some form of sneakers, often basketball sneakers.

This is the actor’s go-to look, especially when he runs on an errand. He never goes too long without wearing this look, and who can blame him? It’s extremely fashionable.

2. Superman Sandler

Adam Sandler always looks comfortable in basketball shorts and a tee shirt. But once in a while, he likes to mix things up, wearing a Superman logo baggy tee shirt.

Although Adam Sandler isn’t playing Superman on the big screen anytime soon, you’ll often see him wearing the big “S” logo on his chest while grabbing a coffee in LA on a Friday afternoon.

Fun fact, Adam Sandler accepted the Favorite Movie Actor Award for “Grown Ups 2” during Nickelodeon’s 27th Annual Kids Choice Awards in 2014 wearing the Superman tee shirt.

3. Puffer Jacket Sandler

Often, you’ll see him wear an oversized puffer jacket and basketball shorts, but sometimes he’ll switch it up a bit and wear a neon green puffer jacket with red-brown khakis and blue sneakers.

Nothing matches or fits, which makes it the perfect Adam Sandler outfit.

Related: what to wear with a puffer vest

4. Uncut Gems Sandler

Sure, the “Uncut Gems” Sandler is not based on the real-life of the actor, but it’s arguably the most iconic Adam Sandler movie outfit of all time. That’s saying a lot.

This Adam Sandler fit is all about showing your wealth and saying, “I belong” while the leather jacket adds toughness that says, “If you come near me, I will slap the sh*t out of you.”

From the Rolex to the rings, Sandler wore nearly half a million dollars worth of jewelry during the set. And don’t forget, those tinted Cartier shades were ultra-cool too.

5. Hoodie Sandler

“Hoodie Sandler” is always a vibe, and he often wears it no matter the occasion because a hoodie makes him very comfortable and casual.

During the “Murder Mystery 2” Red Carpet event, Sandler’s co-star Jennifer Aniston playfully slams his New York Knicks hoodie look that is layered over a pink and blue tropical button-up.

The actress, who was sporting what she called a “work of art” hand-beaded Atelier Versace Couture mini dress, looked starkly different from her co-star, Adam Sandler.

You gotta love Adam Sandler. He’s unapologetically himself.

6. Talk Show Sandler

Adam Sandler didn’t become the uber-popular Hollywood actor and comedian he is by paying too much attention to his wardrobe, even when doing late-night talk shows on TV.

Every time he is announced as a guest on a talk show, plenty of huge media publications will ask the question, “How terrible will Adam Sandler look tonight?”

I suspect he’ll bring another huge T-shirt and flapping jeans next time he’s on TV.

7. Red Carpet Sandler

Every time Adam Sandler goes onto the red carpet, he wears his reliable pair of khaki pants along with an oversized jacket, both of which colors never match.

8. Tuxedo Sandler

Once in a blue moon, Adam Sandler wears a tuxedo. And when he does, he surely cleans up nicely. Who knows, maybe he’s gearing up to play James Bond sometime in the near future.

Okay, maybe not the British 007 but more of an Americanized special agent with an old-fashioned Brooklyn accent that delegates most of his dirty work to other people.

9. Blazer Sandler

The “Blazer Sandler” outfit is the dressed-down version of the “Suit Sandler” look. In true Sandler fashion, you gotta wear the blazer over a graphic tee shirt and jeans.

10. Flannel Sandler

One of Sandler’s most memorable roles is Happy Gilmore in 1996, and you’ll often see him wearing the iconic flannel shirt in the movie. Turns out, he wears flannel often in real life too.

This particular Adam Sandler outfit is actually pretty nice, especially when you combine a simple flannel shirt with a baseball cap. It’s certainly one of Sandler’s “most normal” outfits.

11. Headband Sandler

16 Adam Sandler ICONIC Outfits (With Pictures) - Style and Run (1)

I’m not sure if Sandler’s playing a local pickup game or going to watch the Yankees play, but every time he sports a headband, there’s going to be some sort of Yankees on it.

12. Baseball Cap Sandler

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Still keeping with the Yankees theme, we’ve got the Baseball Cap Sandler. Some days he’ll wear a simple trucker cap, but you’ll often see him sporting a good ol’ Yankees cap.

13. Pink Sandler

Adam Sandler has resembled a walking bag of laundry, but one tee shirt color that is special is pink. In true Sandler fashion, he’s gotta pair the pink tee shirt with baggy shorts.

14. Straw Hat Sandler

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Hats off to Adam Sandler (no pun intended). You’ll see him wearing a large straw hat whenever he goes on a tropical island vacation with his wife and daughters.

15. UGG Sandler

I love it when Adam Sandler wears his UGG boots because he’ll wear them in a way that doesn’t match the outfit at all, with colors clashing all over the place.

But hey, that’s why the “UGG Sandler” outfit works!

16. Old School Sandler

The “Old School Sandler” takes us back to the 90s and is probably the most wearable of the Adam Sandler outfit from all the ones I’ve mentioned so far.

You can’t go wrong with denim jackets and backward snapbacks, can you?

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16 Adam Sandler ICONIC Outfits (With Pictures) - Style and Run (2024)
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