Highsnobiety
Double Tap to Zoom

It’s official: Adam Sandler is a style icon.

The actor has been named the top trending celebrity style star of 2021 according to Google search data, beating the likes of Harry Styles and Doja Cat. The aughts revival is in full force and can be found everywhere from luxury fashion shows to Supreme’s Tiffany collaboration, and Sandler’s carefree, baggy style encapsulates the era perfectly. His uniform of oversized basketball shorts, complemented with an equally huge top, and a pair of colorful basketball sneakers is the ultimate Y2K uniform.

However, it is his indifference to fashion that makes the 56-year-old a true icon. There have been numerous premieres and red carpet events where you can immediately recognize Sandler sporting his usual casual attire, surrounded by a swarm of suave suits. Most famously, his choice of footwear for the premiere of Evan Almighty was a pair of slippers.

Rick Owens reportedly once said: "the coolest thing is when you don’t care about being cool anymore. Indifference is the greatest aphrodisiac — that’s what really sums up style for me." I guess that makes us thirsty for Adam Sandler.

This is only confirming what Tik Tok has been saying for some time. Style-conscious users on the video-sharing platform have been obsessing over the Uncut Gems star's unorthodox fashion tastes and creating their own versions of his outfits. And it isn't just TikTok. Last year Pete Davidson, whose street style has made him the world's most eligible bachelor, revealed that Adam Sandler was his "favorite fashion icon," and we have a theory that he is the inspiration for some of Bieber’s recent outfits

If you want to join in and get some fashion inspiration from the celebrity style star of the year, check out a selection of Sandler’s best looks below. Of course, we have put our own twist on the looks through our shopping suggestions and have brought you some luxury alternatives where possible.

Classic Sandler

This is the trademark Sandler uniform. Without a care for traditional proportions, the actor's oversized, slouched blue basketball shorts finish way below his knee while a contrasting red t-shirt swallows him whole.

Image on Highsnobiety
KENZOPrint T Shirt
$195
Buy at Mr Porter
Image on Highsnobiety
adidasSwingman Shorts
$60
Buy at adidas US
Image on Highsnobiety
GucciAcetate Sunglasses
$317
Buy at Matches

Smart casual

Probably the most wearable of the looks selected, this outfit from 2005 is from Sandler’s hand and footprint ceremony at the Mann Chinese Theater on Hollywood Boulevard, where he joined a host of famous names in leaving their mark in the concrete in front of the building. While most people wore a suit for the occasion, Sandler dressed up well from his usual uniform.

Image on Highsnobiety
'47New York Yankees Classic Baseball Hat
$29
Buy at Urban Outfitters
Image on Highsnobiety
WOOD WOODStriped Shirt
$242
Buy at Matches
Image on Highsnobiety
ICECREAMT Shirt
$30
Buy at Matches
Image on Highsnobiety
LoeweCargo Trousers
$1600
Buy at Mr Porter

Uggs and shorts

While we have all proven to be partial to Sandler’s early-2000s fits, his attitude to dressing has remained constant since then. Ugg boots have become a new favorite of the actor as he continues to prioritize comfort and, in this outfit from earlier in the year, he paired them with his signature baggy shorts.

Image on Highsnobiety
Liberal Youth MinistryCropped Hoodie
$475
Buy at Mr Porter
Image on Highsnobiety
UnsignedLos Angeles Lakers Reversible Shorts
$372
Buy at NBA Store
Image on Highsnobiety
UGGClassic Mini Boots
$130
Buy at StockX

Colour clashing

Turning up at The Late Show with David Letterman in 2008, this colorful outfit shows a different side to Sandler than oversized tops and shorts.

Image on Highsnobiety
Moncler GeniusQuilted Gilet
$1650
Buy at Mr Porter
Image on Highsnobiety
adidasThree Stripes Tee
$35
Buy at adidas US
Image on Highsnobiety
Salvatore Ferragamo5 Pocket Jeans
$790
Buy at Luisaviaroma
Image on Highsnobiety
YuketenKiltie Boat Shoes
$650
Buy at Mr Porter

Want to keep browsing? Head to the Highsnobiety Shop for more products that we love. Highsnobiety has affiliate marketing partnerships, which means we may receive a commission from your purchase.

We Recommend
  • 11 Crisp White Tees to See You Through Spring & Summer
    • Style
  • Myha’la Is in the ‘Industry’ of Pants-Free Personal Style
    • Style
  • Even Adam Sandler Can't Escape Short Shorts Summer
    • Style
  • Even At Church, Justin Bieber Is the King of Casual Dressing
    • Style
  • Maika Monroe's ‘Longlegs’ Press Tour Is Scarily Stylish
    • Style
What To Read Next
  • Paul Mescal Likes His Knits Like He Likes His Shorts: Teeny-Tiny
    • Style
  • How Analog Watches Became the Culture's Favorite Accessory
    • Watches
  • Saucony’s Chunked-up Trail Sneaker Graduated From the School of HOKA
    • Sneakers
  • Kiko Kostadinov’s Lowkey Second Brand Makes a Lowkey ASICS Sneaker
    • Sneakers
  • This Bauhaus Coffee-Making Set Is So Hi-Tech, The Kettle Has Wi-Fi
    • Art & Design
  • ‘Beast Mode’ Fragrances Aren’t Just For Bros
    • Beauty