“I mean, if you’re talking to a normal guy, this could look unexpected,” Guy adds.
“But if you’re talking to guys who are on a Discord channel all day talking about clothes, it’s already a cliché.”
Adding to the outfit’s outsize importance to menswear enthusiasts is that it’s become inexorably tied to a season that is generally both beloved and mocked by the culture at large (see: Christian Girl Autumn or Pumpkin Spice Mania). “You can’t do as many interesting things with shorts and a T-shirt,” says Schlossman, “but as it gets cooler, there’s the anticipation of more layers and more interesting combinations.” This sentiment is so universally known that it’s taken on its own life as a meme, wherein cooler temperatures mean you can “finally start dressing.” Then there’s the ephemerality factor: “The window to wear shorts and a hoodie is so short, and getting smaller by the year,” Schlossman says. “So there’s this fleeting nature that adds to the excitement, and what makes it so memeable.”
This outfit is also a bit of a placeholder for cooler weather. “In our minds, fall starts on September 1st,” says Guy, who lives in the Bay Area where the weather is notoriously fickle. “But it doesn’t actually get colder until mid- to late-October. So this gives you a taste of fall, while still being comfortable.”
Not every coupling of hoodie and shorts, however, ascends to “perfect outfit” status—just look to Pennsylvania Senator John Fetterman, whose baggy gym shorts and droopy hoodies became an emblem of his outsider status in politics. No one would accuse him of being overtly stylish (though that was part of the point), and he has, thus, become fodder for the aforementioned memeability of shorts and hoodie season.
Guy says he tends to only wear hoodies with jeans, but has worn crewneck sweaters and sweatshirts with shorts to achieve a similar effect. A sweatshirt from a brand like Camber, he says, provides the ideal heft for the pairing. “You want it to have some shape to it,” he says, pointing toward the limp look of Fetterman’s outfits as their fatal flaw.
Schlossman agrees, adding that he thinks a rounder shaped hoodie helps create a more pleasing look. He prefers hoodies from the Portland label Bare Knuckles for their wide, boxy silhouette. He has also noticed a certain evolution to the look of late—away from shorter, thigh-baring athletic shorts and toward roomier numbers with more volume and drape. “I guess it used to be big top, little bottom,” he says. “And now it’s the reverse.” He’s also noticed people wearing chunkier hiking boots with shorts, which he calls “fun gorp cosplay,” as an interesting alternative that could carry over into the cooler months.
So while some may mourn the end of another sun-dappled summer, menswear enthusiasts everywhere are breaking out their hoodies and smiling. Their time, at long last, has come.
