ADAM SANDLER’S STYLE is back in the spotlight, thanks to Happy Gilmore 2, proving that his signature look is still as recognizable as ever. For years, the comedy legend’s off-duty uniform of baggy basketball shorts, oversized T-shirts, and beat-up sneakers has been the butt of jokes. Sandler himself has even acknowledged his “goofy clothes,” owning the fact that they’re not cleaned-up. But here’s the thing: that uniform is exactly what makes him a stylish guy in his own right. He doesn’t care about fit checks, trends, or labels. He dresses for comfort, and that’s his power move. And while you might not want to roll up to work in mesh shorts and an XXL tee, there are some practical style tips you can take from his fits. The key is taking Sandler’s comfort-first formula and making it look a little more polished. Here’s how.

Wear Relaxed Shorts

Sandler lives in baggy basketball shorts, and honestly, I get it. I find the baggy shorts look and loose silhouettes not only more comfortable, but also more stylish than slim-cut pants, and that’s been my vibe all summer. Relaxed cuts are stylish because they drape beautifully, move with your body instead of against it, and create a laid-back silhouette that looks effortless rather than forced. The key here is choosing a pair that doesn’t swallow your frame. Go for a 7- to 9-inch inseam basketball short or a relaxed chino short that gives you room to breathe without veering into sloppy workout clothes territory. They work great with a plain tee or polo, and you wear them anywhere you’d normally default to sweats including weekend errands, casual hangouts, even a chill office environment.

Gap 10.5″ Baggy Denim Shorts

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Levi’s 454 Relaxed Fit 10″ Men’s Shorts

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Uniqlo Sweat Wide Shorts | 9″

Russell Athletic Men’s Mesh Pocket Short

Lean Into Chunky Sneakers

One thing Sandler hasn’t given up on is his chunky sneakers, usually New Balances that look straight out of the ‘90s. And while they used to be the punchline of dad style, now they’re a flex. What makes them different is the comfort—you’re getting New Balance’s signature foam cushioning, which absorbs impact and keeps your feet supported no matter how long you’re on them. That’s why they’re comfortable enough to live in all day, whether you’re running errands or on your feet for hours.

They also add some character to an otherwise basic outfit. Wear them with shorts and mid-calf socks if you’re going for that true Sandler vibe, or swap in relaxed jeans if you want a more cleaned-up take. They’re the kind of sneaker that works for coffee runs, travel days, or just pounding the pavement around the city.

New Balance 530

Asics Gel-Kayano 12.1

Nike Zoom Vomero 5 SE SP

New Balance 1906 Utility

Size Up on Tees

Oversized tees are central to Sandler’s uniform, and I’ll admit, I’m with him on this one. A roomy T-shirt feels better than a slim-fit—and when you pick the right cut, it can actually look cooler too. I tend to reach for boxy cotton tees or slightly oversized fits that drape right instead of drowning me. Tucked into shorts, they create a sharper line; layered under an overshirt, they read casual but sharp. Honestly, they’re the kind of everyday essential that make getting dressed easier, and that’s something every guy should have in rotation.

Abercrombie Premium Heavyweight 2.0 Tee

Uniqlo AIRism Cotton Oversized T-Shirt

Carhartt Loose Fit Heavyweight Short-Sleeve Pocket T-Shirt

Buck Mason Toughknit 90s Boxy Tee

Add a Hoodie

Sandler loves a good hoodie, and I can’t argue with him there. A midweight sweat feels incredibly cozy and when it fits slightly oversized, it gives you that same relaxed energy Sandler always has. I recommend sticking with solid colors—something you can throw on with running shorts, joggers, or jeans. It’s the piece I’ll grab for errand runs, casual Fridays, or beer hall.

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ACE Pullover Hooded Sweatshirt

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Champion Men’s Powerblend Fleece Hoodie

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Closing Tips

As a style editor, I’ve noticed more guys leaning into this exact approach: prioritizing comfort while still looking put-together. I think that’s the shift: it’s not about looking messy, it’s about not having to put in so much effort and still walk out the house feeling great about yourself. And I’d rather see a guy in shorts and a big-ass tee he feels good in than a slim suit he’s about to bust out of.

For me, that’s the real takeaway. Menswear today is less about these rigid rules and more about personal comfort. And Sandler proves you don’t need perfect tailoring or the latest designer drop to make a statement. Sometimes, the most stylish move you can make is dressing for yourself—even if that means basketball shorts and a hoodie.

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As the Style and Commerce Editor for Men’s Health, Joseph covers all-things fashion and grooming. Previously, Cheatham was a commerce editor for Spy, and he has written for Travel + Leisure.