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
Shop the Shorts
Basketball-chic.
Slouchy on purpose.
See you on the court.
Just-right jorts.
Cargo for on the go.
Shop Adam Sandler Inspired Outfits
Rugby Shirt + Heels
Shop the Look
Adding to my cart.
Preppy and cute.
A Y2K favorite.
Oversize and sporty.
That reminds me; I need to book a pedicure.
Mules + Basics
Shop the Look
Basics are never boring.
Elevated and easy.
Tailored and cool.
Ready for a pickup basketball game.
Designed to go with everything.
Camo + Ballet Flats
Shop the Look
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
Shop the Look
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
Shop the Look
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.
-
If You Want to Freshen Up Your Shoe Collection, Start With These 33 Sneakers, Kitten Heels, and FlatsSending my apologies to your wallet.
-
Rihanna Just Wore 2025's "Weird" It Flats With Pajama Pants on the Streets of L.A.I've lost count of how many celebrities own these.
-
I Tested TikTok's Favorite Jean Shorts—Here Are the Pairs Actually Worth BuyingSummer’s not over yet.
-
These Are the It Sneakers Celebrities Love to Wear With Baggy Pants and JeansEvery It girl's go-to.
-
Black Sandals Are Nice and All, But in NYC, Everyone Knows This Shoe Color Looks Chicer With White PantsThe unexpected choice is always a winner in this particular city.
-
I Don't Live in Paris, But These Chic Outfits Make Me Feel Like I DoEffortlessly cool.
-
Cooler Than Jeans and a T-Shirt—Everyone With Good Taste Will Wear These 15 Denim Outfits This FallNext time fall styling inspiration runs dry, just reference these looks.
-
Bella Hadid Just Wore the $160 Designer-Passing White Sneakers That Will Sell Out by September 1Hurry, there are only a few sizes left.
