Short(er) shorts for men are having a moment. Some of the city’s most stylish show us how to do it

When “Last Of Us” star Pedro Pascal playfully opened his red Valentino trench to reveal black midthigh shorts and a significant swath of leg at the Met Gala last month, you could hear the internet gasp. Bravo, the outlets gushed; anonymous legions dabbed their brows. Give us more knee!

Pascal isn’t the only prominent guy to embrace the short short of late. Actor Paul Mescal has been rocking positively tiny athletic shorts with a 1970s flavour on his way to and from the gym. In fact, Pascal and Mescal are set to star together in Ridley Scott’s upcoming “Gladiator 2,” which will no doubt feature plenty of glistening male limbs.

But not too long ago, men’s fashion was governed by a set of unwritten rules that didn’t look so favourably on a gentleman showing off his gams.

“When I moved to New York, I heard early on that you never wear shorts in the city,” says the reigning king of menswear and vocal proponent of shorts, Nick Wooster. “When Thom Browne showed short suits on the runway in 2010, it was a note-to-self moment for me. I came back from that show, hacked the pants off a J. Crew suit with scissors and wore it to work at Neiman Marcus with a French-cuff shirt, tie and wingtips, only to get written up for a dress code violation!”

Thanks in part to trailblazers like Wooster and Browne, short(er) shorts for men are enjoying much wider acceptance than they used to.

“In hip hop, oversized shorts, like the long denim ones, used to be in style. There was no way your knees would be showing. That was literally a marker: if they were, we’d be like ‘What are you doing?’” said legendary Canadian rapper and producer Kardinal Offishall. “But now, I wouldn’t go as far as wearing ‘hoochie daddy’ or short shorts, but knees are acceptable.”

The fit here is key. “I’m tall and not necessarily tall and slender; I’m a pretty solid guy. So for me, (fit is) a little bit of a roll of the dice,” he said. “But because hip hop isn’t like it used to be, where everything was mega baggy, if the shorts are a little slim it’s fine. It’s a good time to dress right now.”

Offishall picked up the midthigh, floral-print shorts he’s wearing in our photo shoot on a recent trip to Miami, and describes them as colourful, casual and relaxed. So how does he feel in them? “Knees out, breeze out! So good.”

A general relaxation around shorts has led to men of all shapes, sizes and backgrounds incorporating them into their wardrobes. Most have gone through a phase of trial and error, but everyone at some point has had to ask themselves a very important question: How much thigh should I really be showing?

Parambir Keila, a stylish ER doctor, prefers a tapered short with a little more length for hiding his varicose veins. “My legs are getting old and don’t look as nice as they used to,” he joked.

Keila is given to searching out unique, environmentally conscious pieces, like the shorts he’s wearing in our shoot, which are from a small Italian brand he found on Yoox.com. “I find that pigmented skin goes better with darker, richer colours. I’m always a fan of anything in the range of burgundy to Bordeaux, for both wines and colours.”

For Keila, shorts signal the change of season. “They are a lovely way to remind yourself that you’re in spring or summer, and that’s sometimes really important in a country like Canada,” he said. “It’s nice to change your wardrobe and embrace the seasons.”

Hemlines and colours are just the beginning. As with pants, there is a whole menu of details to deliberate upon before settling on a signature style. Pleats or no pleats? Baggy or tapered? Elastic waist or zip-up? High-waisted or lowrise?

At five foot five and a half, dapper interior designer Jacques Dinel prefers shorts with a high waist, which he says gives the illusion of a longer leg.

“I had my shorts made by my lovely tailor,” he said, pointing to the Frida Kahlo-print ones he’s wearing. “I thought this fabric was super cool. And they’re exactly how I want them, with pleats and roomy pockets, so I can put my hands or wallet in them.”

His shortest pairs are reserved for the beach, where he’s partial to a boxer-style swim short; at the other extreme, he loves to style shorts with a jacket and tie for a nice dinner. Dinel estimates he owns about 50 pairs, which he wears almost year-round. “It’s funny, I don’t get cold in the legs; I get cold in the upper body,” he explained. “I wear shorts with a down jacket and I’m very happy. I like feeling the breeze on my legs.”

Shorts have been popping up more frequently on fall/winter runways, so expect to see them well before and after the dog days of summer, paired with chunkier tops and offered in heavier fabrics. “Give me a big, thick sweater with a pair of shorts in fall; that’s a lovely look for like late September, early October,” said Keila, who tends to pair them with linen button-downs in peak summer.

For the shorts-curious who have yet to commit, there is one thing to know about dressing shorts up: it’s important to select appropriate shoes.

“Footwear is maybe the most important piece of the puzzle,” said Wooster. “The number one rule for me is: no sneakers. It’s an opportunity to wear loafers, wingtips or bluchers with leather, lug or crepe soles. Even a Birkenstock with a sock. That’s the intention that helps to ensure you don’t look like you’re heading to a frat party.” Keila suggests espadrilles (“always such an easy pair”), or brogues designed for warm weather with cut-out details or designed in a breathable material from Italian brand Marsèll.

“If you have a nice pair of loafers and a tan leg, you’re going to look great in shorts,” concluded Wooster. “You’re going to look like summer and that’s a state of mind worth achieving.”

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