For stylish men, summer in the city is an opportunity to show some leg. Last summer, micro shorts with inseams hovering between five and seven inches were ubiquitous. But today, stroll through Trinity Bellwoods Park in downtown Toronto or scroll through the instructive reels of men’s wear creators, and you’ll spot a trend going in the opposite direction: Shin-grazing shorts.
Jack Peros is the co-founder of the Toronto streetwear brand Shirley, which he started with artist Nick Collini in 2021.Shirley/Supplied
Jack Peros is the 24-year-old co-founder of the Toronto streetwear brand Shirley, which he started with artist Nick Collini in 2021. Peros has been wearing a pair of his own design: Ultra-wide, double-pleated Bermuda shorts that balloon out from the waist and fall two inches south of the knee. They’re a bestseller.
“We’re just delivering a super-simple, genderless, basic version of something that I think people are trying to find,” he said.
The brand is made by and for young creatives. The shorts’ design elements – the proportions, fit and hardware details – make them feel modern. But they also reflect an age-old spirit of youthful rebellion that, according to Peros, informs how he and his friends want to dress today. “I think oversized clothes have always been looked at as this ‘bad boy’ thing,” he said. “We’re in a place where people just want to go against the grain.”
Silhouettes expand and contract with the times. Contemporary styles of oversized clothing are rooted in youth culture and streetwear, from the hippies of the 1970s to the hip-hop stars of the 1980s and 1990s to the skaters and surfers of the early aughts.
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“When you look at fashion back in the ‘90s, it was all about this oversized silhouette and fashion that felt super authentic to musicians or actors or designers,” said Joseph Tang, Holt Renfrew’s fashion director. For smart designer options that skew more millennial, Tang’s top picks include a pair of Dries Van Noten silky boxer shorts and baggy cargos from London-based label Studio Nicholson.
Contemporary styles of oversized clothing are rooted in youth culture and streetwear.Shirley/Supplied
Tang thinks the pendulum swing to voluminous silhouettes is, in part, a middle finger to the quiet luxury aesthetic that has beige-washed fashion in recent years. But he also sees it as a remix of skate and surf styles from the predigital era, which has dovetailed with a resurgence of prep.
Jonathan Anderson distilled this sartorial mash-up in his men’s wear debut for Dior last spring, when he sent models down the runway in billowing chino shorts in shades of olive, khaki and sun-washed pink. They were couture versions of the Abercrombie and Fitch shorts elder millennials wore in high school that are being thrifted by Gen Z today.
Young people tend to reinterpret historical styles through a contemporary lens. Marco Valente, a senior men’s wear buyer at Ssense, thinks the return of baggy shorts points to “a yearning for an era where how one dressed signalled something more about their identity within grander cultural contexts.”
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Today, it can feel like the only fashion statement one can make is, ‘I have money and taste. Can you tell?’ For fresh inspiration, Valente said young fashion fans are taking their style cues from a range of historical references such as old magazine editorials, indie movies and hardcore music. “These subcultures always relied heavily on a DIY attitude,” he said, citing Our Legacy’s Capri Cut version and Willy Chavarria’s raver-workwear shorts as pieces that channel these subversive currents. “Many young men at the forefront of this trend have embodied this, albeit with the added factor of the internet.”
For stylish men, summer in the city is an opportunity to show some leg.Shirley/Supplied
Trends trickle up and down between the street and social media at the speed of a finger scroll. As social media has spawned a homogenized look untethered to subcultural affiliation or personal identity, there’s a desire for our style to say something specific about us, and to use clothing as a vehicle for self-expression when it seems like everyone dresses alike.
This summer, it’s big shorts; next, perhaps we’ll be hiking our hems higher. Trend cycles always come back around. But for the moment, maybe a pair of baggy shorts can make us feel closer to who we were when we were still figuring ourselves out.