The men who wear shorts all winter

December 20, 2023

It’s the middle of winter—cold, dark, and a bit glum. The wind whips, the rain stabs; there’s maybe even snow on the ground. A guy emerges through the fog, wearing a pair of shorts. This is not some sort of January mirage. While the rest of us are wearing tights or long johns under our jeans in the freezing weather, there’s a collective of men—who are not on a run—walking around with their legs out, reports the Financial Times.

So dedicated are they to the kneecap exposé, they appear like this in any weather. “It makes me shiver just to look at them,” says Silvana de Soissons, who runs beauty brand Farm Soap Co. in Dorset, England. Postmen collect her ecommerce orders twice a day, and she’s never seen any of them opt for trousers with their uniform. “The Jurassic Coast can be perishing . . . and they’re all out there in beachwear.”

All around the world, icy pavements are stalked by bare, hairy pins. Like a sartorial equator, many guys dress for chilly temperatures north of the belt, but below it you’d think it was scorching. This odd everyman look has even infiltrated the runway: for his Autumn/Winter 2022 collection, Irish designer Robyn Lynch—no stranger to wet weather—proposed chunky Aran knits, gloves, and Donegal-appropriate down jackets with teeny sports shorts.

American rapper Tyler, The Creator, recently teamed a puffer and a furry trapper hat with preppy white mid-thigh shorts that would look at home on a Wimbledon lawn.

But when it comes to shorts, some Millennials cite their own Boomers as inspiration. “I definitely inherited it from my father, who wears them year-round,” says Chris Black, a brand consultant, podcaster and self-professed “avid fan” of all-seasons shorts. Now based in LA, the 40-year-old benefits from the West Coast’s balmy temperatures, but there aren’t many places he wouldn’t wear a pair—only “the aeroplane and a funeral . . . I crave comfort. Like most pleasurable things in life, once you start it’s hard to stop.”

“I feel confined,” says Baby Boomer Kevin Sanders, a 68-year-old living near Newcastle, the famously chilly north-east region of England. They make me feel childlike—I could do yoga or handstands in them

Sanders started wearing shorts daily as an ambulance driver, and they’re still an everyday fixture in his retirement wardrobe: He owns about 20 pairs. “People do make comments. My daughter used to get laughed at school, but it doesn’t bother me,” says Sanders. “I’ve never come home and said, ‘Oh I wish I had put long pants on.’”

David and Stephen Flynn, the enthusiastic twin brothers of Irish plant-based cooking company, The Happy Pear, agree: They wear identical stretch-denim versions from Mish Mash every day. David likens full-length jeans to “wearing a straitjacket”.

The active duo, 43, swim in the sea every day, and while they focus on keeping their core, hands, and feet warm, they say their legs never get cold. They prefer denim shorts as they’re “very robust . . . and they don’t show dirt,” Stephen says.

“If you’re caught in a downpour, there’s half the amount of material to dry off,” says Henry Connell, the 38-year-old co-founder of London-based canned-wine brand, The Uncommon, who is on a mission to wear shorts 365 days this year. “I’ve now got a bit of a reputation in the office. I feel it’s my duty to see it through.” He wears preppy pairs from basics brand AS Colour on repeat.

For those who are so inclined, the right sort of shorts are important—and it’s still possible to get shorts wrong. Indeed, bright prints or colors are a big no-no: “You don’t want to look like a child at a kiddie pool,” says a frequent wearer.

He suggests Patagonia’s five-inch twill baggies as an everyday choice; he removes the outward-facing label for “a more streamlined look”. Length is also key: mid-thigh is preferable. “Longer or looser veers into [actor] Adam Sandler territory,” he says.  Anything shorter should be saved for the sand.

He suggests desert boots or loafers as a smarter—and more stylish — sneaker alternative. Trainer socks and pool slides should be avoided. Confidence, however, is the real must-wear shorts accessory.

Finally, Henry Connell says that he’s got “chicken legs” but has no qualms putting them on show. “If women can wear short skirts everywhere, men should be able to wear shorts,” says Sanders, who also wants restaurants to allow them for dinner. “I take care of my legs, I’ve got a reasonably nice pair for my age. If you’ve got it, flaunt it, I say.”

Research contact: @FT