Skip to content
Vanity Fair Fashion
Fashion

Adam Sandler–Coded Outfits Are Still Going Strong—5 Ways to Style Baggy Shorts This Summer

By Swedan Margen

Adam Sandler–Coded Outfits Are Still Going Strong—5 Ways to Style Baggy Shorts This Summer
Woman wearing a rugby striped shirt with denim shorts. In the middle, Adam Sandler wearing a bright green graphic tee and basketball shorts. On the right a woman wearing athletic blue shorts, a basic white tee, and a cropped button-up.

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

Adam Sandler wearing a patterned polo shirt and blue basketball shorts.

Shop the Shorts

Bdg Star Player Athletic Short

Urban Outfitters

BDG Star Player Athletic Short

Longline Denim Shorts

COS

Longline Denim Shorts

Sr Sport Cotton Gym Shorts

Sporty & Rich

SR Sport Cotton Gym Shorts

Selina Cutoff Bermuda Denim Shorts

Mavi Jeans

Selina Cutoff Bermuda Denim Shorts

Women's 91 Baggy Denim Jort

Cotton On

91 Baggy Denim Jort

Shop Adam Sandler–Inspired Outfits

Rugby Shirt + Heels

A woman standing wearing jean baggy shorts, a orange and blue polo, and yellow heels.

Shop the Look

Colorblock Cotton Rugby Shirt

Polo Ralph Lauren

Colorblock Cotton Rugby Shirt

Long Sleeve Rugby Polo Shirt

Madewell

Long Sleeve Rugby Polo Shirt

Tori Kitten Heel Sandal

Open Edit

Tori Kitten Heel Sandal

Hanna Stripe Rugby Shirt

EDIKTED

Hanna Stripe Rugby Shirt

Lock Sandal

That reminds me; I need to book a pedicure.

Mules + Basics

A woman wearing blue athletic shorts, a white tee, and cropped button-up.

Shop the Look

Fitted T-Shirt
Lock Loafer Mule

Kelsi Dagger Brooklyn

Lock Loafer Mule

Stripe Long Sleeve Crop Poplin Button-Up Shirt

MANGO

Stripe Long Sleeve Crop Poplin Button-Up Shirt

Mesh Basketball Shorts

PacSun

Mesh Basketball Shorts

Ready for a pickup basketball game.

Flat Mule

Designed to go with everything.

Camo + Ballet Flats

A woman on a bike wearing baggy camo shorts, a white one-shoulder blouse, and yellow Tabi flats.

Shop the Look

Missouri Camo Low Rise Long Shorts

BDG

Missouri Camo Low Rise Long Shorts

Cool without trying too hard.

Alohas Gill Mesh Ballet Flats

Alohas

Gill Mesh Ballet Flats

Mesh flats look so chic in the summer.

Regimen Ankle Wrap Sneaker

Jeffrey Campbell

Regimen Ankle Wrap Sneaker

Ballet-sneaker flats are everywhere, and I love it.

Camo Low Rise Cargo Bermuda Shorts

EDIKTED

Camo Low Rise Cargo Bermuda Shorts

Blend right in with the fashion crowd.

Ria Ruffle Top

BDG Urban Outfitters

Ria Ruffle Top

Ruffles are calling my name.

Baseball Cap + Bag Charms

A woman standing wearing baggy shorts, a flannel, a baseball cap, and sneakers.

Shop the Look

Men's New Era Olive New York Knicks Tonal Florals 59fifty Fitted Hat

New Era

New York Knicks 59fifty Fitted Hat

The Sabremoji Fruit Charm

MAISON de SABRÉ

The Sabremoji Fruit Charm

Need to add to my bag-charm collection.

Beaded Necklace Bag Charm

Free People

Beaded Necklace Bag Charm

Saylor Poplin Pull-On Shorts

Free People

Saylor Poplin Pull-On Shorts

Syracuse Baseball Cap

Sporty & Rich

Syracuse Baseball Cap

Love a good baseball cap.

Studded Belt + Pop of Color

A woman standing wearing white baggy jean shorts, a studded belt, a leather jacket, and yellow sneakers.

Shop the Look

Samba Og Sneaker

The OG Sambas with a twist.

Tokyo Shoes
Rhodes Stud Belt

Free People

Rhodes Stud Belt

A good belt really brings a look together.

MANGO, High-Waisted Straight-Fit Denim Jorts

MANGO

High-Waisted Straight-Fit Denim Jorts

Dara Faux Suede Hobo Bag

JW PEI

Dara Faux Suede Hobo Bag

Originally published by whowhatwear.com. Syndicated material does not necessarily reflect the views of Vanity Fair Fashion.

More Fashion