Spotted on the streets of NYC, courtside at the Knicks, or on the red carpet, Adam Sandler is always reliably his authentic self. Sandler has achieved what every fashion person in New York wants: the ultimate unbothered, effortlessly chic, cool-girl closet.
On days I want to feel casual and sporty without trying too hard, I channel my best Sandler by styling a pair of jorts or athletic shorts with an oversize tee or just experimenting with accessories. There’s no denying he’s a funny guy, but over the past few years, his fashion sense has become something people genuinely love. No surprise his style influence is having a resurgence this summer.
So here are some of my favorite ways to style Sandler’s iconic baggy shorts. And of course, we’ll start with some very “Adam Sandler chic” shorts options.
Adam Sandler Inspired Shorts
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Basketball-chic.
Slouchy on purpose.
See you on the court.
Just-right jorts.
Cargo for on the go.
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Rugby Shirt + Heels
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Adding to my cart.
Preppy and cute.
A Y2K favorite.
Oversize and sporty.
That reminds me; I need to book a pedicure.
Mules + Basics
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Basics are never boring.
Elevated and easy.
Tailored and cool.
Ready for a pickup basketball game.
Designed to go with everything.
Camo + Ballet Flats
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Cool without trying too hard.
Mesh flats look so chic in the summer.
Ballet-sneaker flats are everywhere, and I love it.
Blend right in with the fashion crowd.
Ruffles are calling my name.
Baseball Cap + Bag Charms
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Next year is our year.
Need to add to my bag-charm collection.
IYKYK.
Chic and comfortable.
Love a good baseball cap.
Studded Belt + Pop of Color
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The OG Sambas with a twist.
A vibe all on its own.
A good belt really brings a look together.
Sleek and simple.
Go-to hobo bag.
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I Thought Wearing These Shoes With Shorts Was Cringey—Turns Out the Combo Is Peak 2025Apologies are in order.
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