This Is How I Win
Adam Sandler Is Gen Z’s Definitive It Boy
Between You’re So Not Invited To My Bat Mitzvah’s success, the endless virality of Uncut Gems, and Sandler’s fashion icon status, the comedian has found a whole new generation of fans.
Among the pantheon of Gen Z fashion icons, there are some fairly predictable patterns. You have your nepo babies (Sofia Richie Grainge, Hailey Bieber), your Pete Davidson exes (Ariana Grande, Chase Sui Wonders), your nepo babies-slash-Pete Davidson exes (Kaia Gerber, Margaret Qualley, Cazzie David). But another name, the one-of-these-things-is-not-like-the-others name, has also loomed large in terms of cool-kid outfit inspo for the last few years. I’m speaking, of course, of comedy legend and bona fide style inspiration Adam Sandler (who also happens to be a close personal friend of Pete Davidson).
As of publication, the phrase “Adam Sandler Summer” has 2.6 billion views on TikTok, and elsewhere on the platform, the band Haim uploaded their own video celebrating the idea of an Adam Sandler summer. “Shorts to your knees / big-*ass graphic tees / sneakers if you please / b*tches guaranteed,” they sang. And mainstream media — from Vogue and InStyle to Highsnobiety and Esquire — have gone so far as to have dubbed Sandler a style icon. (Albeit, as Esquire put it, a schlub style icon.)
But it’s more than just the fact that Sandler’s style — idiosyncratic, comfortable, and likely made up of items plucked from the way back of his closet — is now en vogue. It’s that the actor himself has caught on with the generation born after Billy Madison came out, with a survey of 100,000 teenagers even naming Sandler their favorite celebrity.
When you think about it, it’s not surprising. Uncut Gems memes (“This is how I win”; “Uncahhh Jaaams”) have dominated the internet since the movie was released in 2019. Sandler’s constantly in the press for chaotic good reasons, like casually playing a game of pickup basketball with Timothée Chalamet. And his most recent film, the family-friendly You Are So Not Invited To My Bat Mitzvah, was recently Netflix’s number one movie in America, and the third most popular globally. Why wouldn’t Gen Z embrace Sandler as their definitive It Boy?
There’s an argument to be made that every generation decides what’s popular in direct retaliation to the generation that came before: Reaganite Yuppies were a response to hippies; musicians turned to grunge in the ’90s to counteract the makeup-and-hairspray hair metal and glam rock of the ’80s. So naturally, Gen Z has found their own way of rebelling against their predecessors: millennials.
If one thing embodies the millennial mindset, it’s trying hard. We were the generation of girlbosses and hashtags, of peplum skirts and meticulously-constructed sock buns, an era best embodied by Zooey Deschanel playing the ukulele and wearing Etsy-ready poodle skirts. And I will be the first to admit: It was cringe! It remains cringe! Earnestly trying hard — caring a lot about anything, actually — is the foundation of what makes anything cringe.
Gen Z, on the other hand, has replaced girlbossing with quiet quitting. They prefer casual photo dumps over the filtered and color-curated Instagram posts of my youth. And Sandler is the personification of this ethos: choosing to do less, be comfortable, and have a good time.
But here’s the thing: If Sandler is cool (he is), it’s because he’s also authentic in his choices — both style and otherwise. Sandler dresses like he’s always moments away from a pick-up basketball game because he is always moments away from a pick-up basketball game. (Again, probably with Kylie Jenner’s bf!) His style also isn’t artifice: It’s completely unaffected by trends, by time, or by his millions of dollars. Sandler looks like he doesn’t really care about clothes because he very likely doesn’t.
So rather than see the Sandler aesthetic as a trend to chase and achieve, the best way of embracing Sandler-dom is to dress exactly the way you want to dress, regardless as to whether it’s considered trendy or not. Because while the world has changed around him, Sandler (unproblematic king) knows exactly who he is and what he wants to wear. As a cringey millennial, that’s the inspiration I’m chasing.