Adam Sandler is the king of dad jokes and dad style. The American comedian has been making us laugh for over three decades, since coming up on SNL in the early 90s. From there, he went on to star in some of the decade’s defining comedies, like Happy Gilmore, The Wedding Singer, Mr. Deeds, and 50 First Dates, and even some of this century’s most iconic indies, including Uncut Gems and Punch-Drunk Love.
However, Adam’s defined more than just the zeitgeist of early 21st century comedy. He’s also become one of most unlikely but influential style icons. Following the COVID pandemic and the rise of the ‘infit’, the Gen X actor became 2021’s top search in Google’s celebrity style category, spawning TikTok hashtags and think-pieces alike. During a time when we were asked to shelter in place (and worry about things much greater than mere fashion), Adam’s laid-back, loungewear-first approach to style became not just appealing but genuinely aspirational.
For 30 years the actor has stuck to his sartorial guns, wearing a rotation of tried-and-true slacker staples including denim jackets, baseball caps, oversized graphic tees, bowling shirts, baggy shorts and track pants, and sporty sneakers. In the actor’s own words: “I wear the XXL shirts. I wear the XXL shorts. I pull my socks up goofy and I wear my sneakers.” Here, we look back at some of the comedian and unexpected style star’s most iconic outfits from the 90s to now.
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At the ‘City Slickers II’ premiere, 1994
Before becoming Hollywood’s go-to comedic lead, Adam got his start on the iconic late-night sketch show Saturday Night Live. Initially, Adam was hired on the show as a writer, before becoming a featured player in 1991. During his four year-long SNL career, Adam brought us classics such as “Lunch Lady Land.” Here, during his freshman year as a featured player, Adam attends an SNL cast party in one of his signature early 90s looks: a Canadian tuxedo, a casual print tee and backwards baseball cap.
At LAX, 1998
Wondering what the king of casualwear wears to the airport? Look no further than this 1998 LAX outfit consisting of one track jacket, one graphic tee, a pair of sweatpants, and some rather snazzy-looking suede sneakers.
At a party for The Wedding Singer, 1998
After being fired from SNL in 1995, Adam became the face of 90’s screwball comedy with blockbusters including Happy Gilmore, The Waterboy, and Big Daddy. Among the best of them was 1998’s The Wedding Singer, in which Adam stars as the titular vocalist opposite Drew Barrymore. Here, the co-stars attend a party for the film’s launch at New York’s Planet Hollywood. For the occasion, Adam wore his signature sweaters and baseball cap alongside a Planet Hollywood-branded leather jacket.
At the Superbowl, 2004
In 2004, Adam and Drew joined forces once again for romantic comedy 50 First Dates. The film, which takes place in Hawaii, centers on the budding romance between a veterinarian (Sandler) and an amnesiac art teacher (Barrymore). Adam embraced the film’s tropical locale during its press run, opting for Hawaiian shirts — like this one — rather than his usual long sleeve button-downs.
At the Mann’s Chinese Theatre, 2005
This is it: the quintessential Y2K Sandler fit. Here, while forever cementing his hand and foot prints in a ceremony outside Los Angeles’ Mann’s Chinese Theatre, the comedian wears his signature graphic tee-and-button down combo with a pair of relaxed slacks and colorful sneakers. Some things never change.
In Los Angeles, 2015
This is Adam Sandler in his main mode du jour: baggy T-shirt and even baggier basketball shorts. But did you know that Adam is one of the OG UGG-fluencers? The comedian rocked UGG Minis way back in 2015 — nearly a decade before Bella Hadid launched the style’s 2022 revival.
In Uncut Gems, 2019
In 2019, Adam transformed into fast-talking diamond dealer Howard Ratner for the Safdie brothers’ Uncut Gems. The transformation came courtesy of wunderkind stylist Miyako Bellizzi and Mordechai Rubinstein who modeled the look after three real-life Diamond District dealers. Throughout the film, Howard wears a medley of sleazy looks featuring gaudy pieces from luxury brands like Hugo Boss and Missoni. The character’s most iconic outfit arrives in the film’s chaotic opening sequences, and comprises of double-pleated Zegna pants, Ferragamo leather goods, and a mustard Theory polo sourced from Century 21 that’s “so thin, you can kind of see his nipples through it,” Bellizzi told Vogue. Dreamy!