Readers’ Vote: Which Of These Adam Sandler Outfits Belongs In A Hall Of Fame

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.

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.

There’s nothing as attractive as a man who loves his wife, even if he teases her sometimes. That was presumably Adam Sandler’s intention with this “Happy Birthday Jackie” tee, featuring his wife’s baby photo.

Unlike most of his closet, this is a custom-made piece. Adam presumably had a shop make this t-shirt for him so that he could surprise his wife with it. We’re genuinely shocked that this cute fashion moment didn’t get more attention.

This might not be a full red-carpet formal, but Adam looks quite dressed here. He may have traded out his sweatpants for the event, but we’re pleased that he is still dedicated to polos.

His sunglasses complete the look, proving that you don’t need to go over the top with accessories. Fans have always gone wild over his on-screen shades, so it’s good to see appreciation off-screen, too.

One of the best things about an unserious A-lister like Adam Sandler is that fans don't question odd photos of him. He can eat a jar of pickles on the street, but nobody will comment. But we would like to mention his stylish red scarf.

His long wool coat is another rare high-fashion moment, given that Sandler’s winter gear usually includes oversized puffer jackets. This is quite a tame look, so we’re glad he added the pickles to make it a classic #Sandlercore moment.

This is, without a doubt, one of Adam Sandler’s most iconic outfits. He wore it back in 2014 with some staple oversized blue basketball shorts, unlaced sneakers, and dark glasses. What seemed like a routine coffee run turned into an OG fashion moment.

The baggy Superman shirt has been a trend on TikTok for years, and the actor has been seen wearing it several times since, always paired with oversized shorts or sweatpants. Sandler recycles his wardrobe and happily rewears his favorite pieces, unlike many stars.

When people think of Adam Sandler’s outfits, they always bring up casual t-shirts and big shorts, but he has occasionally embraced formal dress codes. For the 2025 “SNL 50: Anniversary Special” episode, Sandler donned a sharp tuxedo as he took to the red carpet alongside his wife, Jackie.

Though he joked to Variety that wearing the tux was a “terrible experience” compared to his usual garb, he explained that he dressed up because he was asked to. Fans found the look unusual, but its rarity makes it one to remember.

Sandler’s closet has many pairs of track pants, but his most famous are the red Adidas ones he wore for a 2024 interview with Jimmy Fallon.

Fans were thrilled to hear the comedian spill details about Happy Gilmore 2, and equally pleased to see him maintain his casual look even on late-night TV. His red Adidas track pants became the star of the show.

Who said that men can't wear UGG boots? Adam Sandler didn’t let them stop him when he was pictured out with his wife in Santa Monica in January 2023, sporting a pair of suede boots and giving Bella Hadid a run for her money.

But what really made the outfit iconic was his choice to pair them with a floral shirt, basketball shorts, and fleece. This unlikely mix of contradictory items perfectly captures his mismatched style; some even call him UGG’s true ambassador.

Adam Sandler’s costume in Uncut Gems is one of the most famous in recent years. He wore a leather trench coat, a yellow polo shirt, gray trousers, and a matching belt and loafers. His specially-designed accessories included a diamond-encrusted Rolex and several chunky rings.

GQ named Sandler’s character Howard Ratner the “most stylish character of the year” in 2019. Critics raved about his performance in the movie, but his outfit sealed the deal for fans.

Adam Sandler has a fun tendency to pair bold shirts with pants that don’t match them, yet he always makes it work. His fans have declared him a fashion icon, a title that he politely laughs off because he only wears “goofy clothes” (per People).

But that’s precisely why Gen Z loves his look.

This floral shirt might be eye-catching, but it doesn’t seem to clash with his baggy shorts and basketball shoes. It’s proof that Sandler can grab random items from his closet and go instantly viral.

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.

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.

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.

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.

It’s old, but this crop top is iconic because it ignited the “Madam Sandler” TikTok craze, which sees women “paying homage to the actor’s signature look,” according to Today. It’s certainly a look that deserves to be remembered.

In 2021, Sandler changed the memeification game by dressing as a meme. He wore a “You Mad?” troll face tee, paired with a hoodie and his classic baggy shorts.

This outfit is fun yet straightforward because it showcases the actor’s unserious approach to clothing. He picks what he likes, not what fashion magazines would like, and that’s pretty refreshing to see.

This is the picture of Adam Sandler that everybody should see at least once. We almost didn’t notice the Y2k purse because of his clashing pink t-shirt and, red shorts, and quirky sunglasses.

But the purse makes the look, even if it looks expensive compared to the rest of the outfit. We’re unsure if the purse belongs to Sandler, but we appreciate how unapologetic he is about toting it around.

If anybody else wore this, it wouldn’t work, but it does for Sandler. His fans don’t bat an eye when he wears a baseball cap, but this wide-brimmed, safari-style hat changes things.

In true Sandler style, the hat has nothing in common with the rest of the outfit, which includes a plaid shirt and sporty sneakers. The hat should be included in the next round of Sandler TikTok cosplays.

He’s had his fair share of chaotic moments over the years, but even Adam Sandler hadn’t crashed a wedding until 2018. He wore a classic t-shirt and shorts combo, but still looked good in the wedding photos.

The couple looks thrilled to be photobombed, and even Adam’s divisive moustache doesn’t detract from the photo. It’s a fun moment that highlights how Sandler doesn't take life too seriously.

Adam Sandler dresses like a basketball player but enjoys the sport like any other fan. In 2023, he proved his dedication to his team, the NYC Knicks, on the red carpet with Jennifer Aniston.

Unlike his glamorous co-star, Adam didn’t dress up for the occasion, but at least his hoodie wasn’t ridiculously oversized. There’s even a fun, floral-patterned Sandlercore easter egg for fans peeking out at the bottom of his sweater.

Another of Sandler’s sartorial strengths is his ability to wear oversized athletic gear as everyday street wear.

According to UNILAD, he confessed on a podcast that he began wearing those clothes because he “used to be jacked” and liked to surprise people. Now, he prefers them for comfort.

In this candid, belly-flashing snap, he pairs a well-worn tee with knee-length Adidas shorts and sneakers. He wears so many Adidas that in 2021, the brand released a Happy Gilmore line despite having never worked with Sandler.

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.

To some people, Adam Sandler’s crimes against fashion involve wearing workout gear and Nike shoes on talk shows (ahem, Jimmy Fallon). But we’d like to redirect attention to this picture where he rocks triple denim.

Strangely enough, it works. The jeans, shirt, and jacket are all different shades, so they contrast each other, and the early 2000s lighting also works with this look. It's certainly one for the memory book.

While the neon green puffer is a well-loved icon, this XXL Adidas coat deserves some attention, too. The comedian made another fun contrast with this outfit by pairing a ridiculously big coat with shorts and bare legs.
According to GQ, Sandler’s process for buying clothes is simple: He just “takes his 'normal size' and goes one or two sizes bigger.” This Adidas jacket is comically large, but for Sandler, comfort beats out style on any day.

Adam Sandler has been acting since the 80s, but his lovable dad looks always eclipse his younger looks. This picture, which features the actor in a beanie and sleeveless tee, is a good example of his early style.

It might not be wacky enough to go viral, but many fans wouldn’t even recognize Sandler in this photo, so we had to share it. He’s even wearing some jewelry, which he rarely does in his current outfits.

While Sandler may have declared himself “ripped” back in the day, he has no qualms about poking fun at his current body. According to People, he once joked that he wears XL clothing because he “had pizza at Clooney’s house”. But his fans don’t see anything to joke about.

Dad bods are back in, which explains why this picture was shared so much. The swim shorts aren’t special, but it was a rare moment of Sandler actually dressing for his surroundings, and many fans enjoyed the view.