The men who wear shorts all winter

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. 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. 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 autumn/winter 2022, 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.

Fashion is all over the dad trend: chunky sneakers, baggy stonewashed jeans, sweater vests and fleeces have all been co-opted by younger crowds. 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.” 

Curious about this intergenerational commitment to the cut-off — which for me would induce mottled, blue-tinged thighs and guaranteed chilblains — I asked some dads why they are never inclined to cover their calves. “I feel confined,” says 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

He 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. “They make me feel childlike — I could do yoga or handstands in them,” says David, who 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. “They’re practical, not fashionable.”

Pip Quartermaine, a 63-year-old veteran of the British parachute regiment from Leamington Spa, also enjoys shorts’ functionality: he says cargo styles, bought from army surplus stores, are best for storing wallets and car keys. He wears them with a fleece and Skechers.

Shorts are preferable in the rain, too, as skin is naturally waterproof. “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.

From a style perspective, Gerard Robertson, a 51-year-old civil engineer from west Scotland, struggles with smart-casual dress codes, and says cargo shorts in chino fabrics are an easier option for everyday. “I feel like I have to tuck my shirt or T-shirt in when I wear trousers, and I feel a bit silly wearing trainers with nice full-length pants.”

Billy Redden, a 40-year-old office worker and former rugby player from Cumbria, also finds shopping a challenge: at 6ft 3in and 19 stone, he finds that trousers are problematic for his thigh-to-waist ratio. “Big legs don’t work well with jeans,” he says. And menswear, according to Robertson, lacks options. “Women get clearly different styles but there’s not enough variety [of trouser silhouettes] for us,” says Robertson.

Specifics are important — and it’s still possible to get shorts wrong. LA-based Black, who recently wore shorts as part of a Thom Browne tuxedo to the GQ Men of the Year party in Los Angeles, says that bright prints or colours are a big no-no: “You don’t want to look like a child at a kiddie pool.” He suggests Patagonia’s 5in 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 Adam Sandler territory,” says Black. 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. 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.” 

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