Ready for short shorts, guys?

Dedicated readers might recall that this time two years ago I pleaded with my fellow men to “free the knee” and give tailored shorts a try. Now I’m back, and things are getting positively racy. With smart shorts mastered, it’s time to go further and “free the thigh” – if you dare.

Short shorts have made an unashamed return to men’s fashion. Whether printed at Thom Browne, wide-legged and pleated at Hermès or checked and sporty at Dior, the SS23 runways showed plenty of upper leg. The same applies to swim shorts. British resortwear stalwart Orlebar Brown launched in 2007 with one classic style in four different lengths, the shortest of which, the Springer and the Setter, both cut off at mid-thigh. “They are increasing in popularity,” says founder Adam Brown. “People like a shorter length for an occasion that is a little smarter, when matching swim shorts with shirts, or just looking to show a little more leg.” 

French brand Vilebrequin has always championed shorter styles, tied to its origins in St Tropez in the ’70s. “The inspiration came from surfers,” says CEO Roland Herlory. “The founder of Vilebrequin created a European style; the shorts weren’t long, and they weren’t worn to protect the legs. They were designed to be comfortable and seductive.”

Vilebrequin’s Short Classic trunks are true to the proportions of the retro originals. I own two pairs in block shades, which are less showy than busy prints. While subtly shorter, they’re not for exhibitionists; they are simply neatly cut, flattering shorts that look smarter than old-fashioned trunks.

“Your swim shorts say a lot about who you are,” Herlory adds. “They are the most liberating and best for tanning – but I think it says a lot about the confidence of a man who chooses to wear a shorter style.”

It’s all very well advocating for shorter shorts for the beach and by the pool, but can the same logic apply in town? Contemporary Australian brand Haulier launched in 2020 with its cult-favourite Utility totes, but has since expanded to a full-look offering, stealing the show at Australian Fashion Week this year. To founder and creative director Jeremy Hershan, the brand’s two types of short shorts, which reference classic sailing and track styles, are easy to style when the sun’s out.

Confidence is sexy and short shorts are the embodiment of this

“The Haulier wardrobe takes inspiration from the athletic-wear of decades past, as well as military, workwear and tailoring influences,” says Hershan. “I love the idea of mixing traditional codes of dress for an irreverent outcome. The Harmony Sailing shorts and Monaco Track shorts embody the wandering free spirit of the brand. They’re best worn short and mixed with the aforementioned influences.” For SS23, Haulier’s collection pairs sporty shorts with classic T-shirts and preppy blazers, fisherman’s sandals and brightly striped Western shirts. The look is lighthearted and eclectic – and that’s the point.

Haulier velour Harmony sailing shorts, £130

Orlebar Brown recycled nylon Springer swim shorts, £195

Dior linen-mix shorts, £1,550

Community Clothing cotton pleated shorts, £70

“Growing up in Australia, short shorts are somewhat second nature,” adds Hershan. “They bring to mind the imagery of Australian photographer Rennie Ellis and they’ve been championed by sportsmen and rock stars alike.” He also references a favourite photo of AC/DC taking a load off on tour in Rio de Janeiro in 1985. “Confidence is sexy and short shorts are the embodiment of this. Try them at home, try them for sport, try them poolside and for the occasional errand. Before you know it you’ll be a convert.”

Of course, there are limits. Patrick Grant, designer and creative director of Community Clothing, both makes and wears “work shorts” that pair a mid-thigh length with military-inspired patch front pockets, but he doesn’t see them making it into the office yet. “In that context it still feels anathema,” he says. 

“But, there are a lot of guys out there who are happy to show off their physique in a way that’s a bit braver than it has been for the past 15 or 20 years. In my lifetime of being interested in clothes, I’ve seen shorts go from really short, to really long and back to really short again. Tailored shorts that fall two-to-three inches above the knee are perfect for padding around the shops on a Saturday. Keep your top loose, and wear a shirt or long-sleeved crewneck, just so you’re not all bare flesh.”

While wearing above-the-knee styles might be daunting, Brown makes a compelling case for raising hemlines. “There are many subtle things that make men look and feel good,” he says. “A shorter style can make the leg look longer, with more shape. It’s a simple change that many will be pleasantly surprised with.” They might take some getting used to at first, but when the heat’s on, it pays to get shorty.