Whenever it seems the actor Adam Sandler has achieved Maximum Sandler Fit, featuring a dizzyingly comfortable combination of athletic clothes and high-leisure vacation wear, he always manages to one-up himself. “You are your own best competition,” or however the appropriate idiom goes.
This week, Sandler went on a rainy-day jaunt with his wife, Jackie, to Brentwood Country Mart in Santa Monica, wearing what at this point the internet would classify as a classic Sandler Fit: an olive green Columbia zip-up fleece over a floral Hawaiian shirt, a flowy pair of peach-bellini-orange basketball shorts, and his well-loved pair of chocolate-brown classic mini Ugg boots.
That Sandler manages to perform new clothing alchemy, yielding new formulas while recycling the same old elements, is part of his frumpy magic. (That, or an entirely pure lack of self-consciousness.) His shoes of choice—Hoka running sneakers, nearly overcooked Uggs sans socks—convey an aggressive practicality, a staunch prioritization of comfort. Uggs, before their princess-sleaze rebirth in the early 2000s, were designed for pragmatic warmth; the brand initially marketed them as an après-surf shoe after a surfer in 1970s Malibu pulled on a pair of Australian sheepskin boots following a chilly day hitting the waves. Uggs tend to look their coolest when worn in this tradition: throwing on a real beat-up pair with whatever else you’ve got on to go grab the daily newspaper from off the sidewalk or make the trek from the sand to the boardwalk. (Depending on your luxury metric, this logic could also be used to explain the appeal of Mary Kate Olsen’s scratched-up Hermés Kelly bag.)
Given their surfer origins, maybe this is also why Uggs look so cool with shorts, which brings us to another menswear alchemist and notable Uggs wearer, the supermodel Bella Hadid, whose big fit from last year—moto jacket, white micro shorts, platform mini Uggs, slice of pizza—apparently caused searches for similar Uggs to jump 152% in a single day, according to data from Lyst.
These days, personal style, both on the internet and in the industry at large, can feel like a sprawling gated community of disparate cottage industries. Bin a certain corner of the fashion industry (or fashion TikTok, populated by words and phrases like “quirky” or “y2kcore”) you may find Bella Hadid and Adam Sandler occupying the same intersection in the proverbial Venn diagram of contemporary fashion.
