Unbelievable! Which Adam Sandler Outfit Shocked Fans Enough to Earn Hall of Fame Status?
Adam Sandler wore a navy blue suit to the 2020 Emmys in another rare formal moment. True to form, it was oversized and untailored. Some questioned why he would choose an ill-fitting suit, whereas others said it was on-brand.
He wore the same suit (plus a moustache) to the Independent Spirit Awards that year, where he won Best Male Lead for “Uncut Gems.” The repeat made the outfit feel even more in-character.
Adam Sandler really is just like us. He’s often seen in plaid flannel shirts, a wardrobe staple for many people, but this picture with his dog, Meatball, is particularly special. His English Bulldog even served as ringbearer at his 2003 wedding before sadly passing away a year later.
Sandler’s plaid shirts don’t get much attention, but he regularly wears them in different colors. In this photo, however, Meatball takes center stage.
Only Adam Sandler could effortlessly pull off so many clashing items and create a finished look that works. His red Adidas track pants (likely the same pair he wore to Jimmy Fallon) are right at home at a basketball game, but don’t miss that Hawaiian shirt peeking out from under his jacket.
But Fat Joe’s fabulous pink velvet puffer jacket stole the show in this photo. It looks like something that Sandler himself could also rock.
This neon green puffer jacket needs no introduction. GQ Australia even christened him a “sartorial soothsayer” after he wore it leaving Good Morning America in 2023.
Fans can add the North Face jacket to their closets to channel Sandlercore. It looks even better with Sandler’s signature bold shirt peeking out underneath.
Sandler may favor XXL, but looks extra small in this image with Serbian basketball legend Boban Marjanović. The two teamed up for the Netflix movie ‘Hustle’, where Sandler’s character was similarly dwarfed by the 7’4” player.
According to Time Magazine, Hustle was “a passion project for Sandler”. Given his love for a baggy t-shirt and baggier basketball shorts, we can see why. Fans love how his movies are fun, especially when he incorporates his famous style.
Anyone who watched the 2025 Oscars will know this next outfit. Sandler wore a bright blue sweater, this time as part of a comedy gimmick. During his monologue, host Conan O’Brien heckled Adam for his dress sense, and the actor quipped back that he loved his “snazzy gym shorts and fluffy sweatshirt”.
Sandler capped off the gag by storming out, but not before giving Timothée Chalamet a quick kiss on the cheek! For many fans, it was the highlight of the night.
On top of its quotable lines, Grown Ups 2 is known for Sandler’s casual striped shirt, worn by his character, Lenny. It might be a plain stripey tee from anywhere, but that’s what fans love about Sandler’s style.
While some criticize the actor for “playing himself” in movies, others love how recognizable he is on screen. He’s now the king of comedies and striped T-shirts.
As if we couldn’t love Adam Sandler more, he’s also a proud girl dad. He has honored his daughters several times through his attire, though only the most eagle-eyed fans have noticed.
The most obvious reference is his hot pink Under Armour Curry “Girl Dad” sneakers. He even wore them to the 2025 Venice Film Festival. His biggest fans know he owns many pairs of Steph Curry’s shoes, but these are special.
If there are two things we know about Sandler’s wardrobe, it’s that he loves Hawaiian shirts and basketball shorts. In this picture from his 2024 GQ Sports shoot, Sandler pairs the two items, creating an interesting contrast.
His signature long basketball shorts have inspired many people to wear similar shorts and jorts, but nobody else can rock this combination. The crew socks are the cherry on top of this mismatched fit.
His signature long basketball shorts have inspired many people to wear similar shorts and jorts, but nobody else can rock this combination. The crew socks are the cherry on top of this mismatched fit.
In the ’90s, Sandler won hearts as the titular character in Happy Gilmore, and most moviegoers would know his iconic jersey anywhere. Many people on TikTok have cosplayed the character and tried to replicate the jersey.
Unlike movies with outrageous costumes, fans love the Happy Gilmore jersey because it combines aspects of both golf and ice hockey apparel. It’s also a nice nod to Sandler’s own sense of style.
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Even before being a mainstream Hollywood star, Adam Sandler made waves. For his 90s movie Airheads, he wore an iconic crop top. This picture shows how much the actor has grown since then.
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