Photo: Orlebar Brown

Historically reserved for warmer climates or as beachwear, the trend of men wearing shorts only started shortly after the second World War, when soldiers in tropical climates wore them for comfort’s sake. Even then, it was seen as a kind of uniform for certain sports and recreational activities or as semi-formal wear for boys.

It wasn’t until the 1950s did it become fashion commodity, thanks to the likes of Marlon Brando and other leading Hollywood men who were seen wearing them. The trend of wearing shorts to social gatherings peaked in 1970s—otherwise known as the decade where anything goes. From cut-off denim shorts to athletic shorts and dress shorts, men were seemingly flaunting them everywhere.

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In the ’80s and ’90s however, when the economies in most parts of the world were experiencing growth followed by a recession, men went back to traditional suiting—mostly in blacks, greys and sometimes camel—and the trend of wearing shorts went back to being reserved for summer vacations.

Thom Browne Fall/Winter 2007
Photo: Getty

The trend resurfaced again in 2007, when Thom Browne sent male models down the runway in short suits. The year after he was named menswear designer of the year by the Council of Fashion Designers of America (CFDA). Although it became part of Browne’s eponymous label’s identity, it wasn’t a popular choice for men.

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Valentino Spring/Summer 2021
Photo: Showbit

Recently, however, the idea of shorts for men, and more specifically, short suits for men have been revived by the likes of Pierpaolo Piccioli for Valentino and Chanel-owned Orlebar Brown—a British menswear and lifestyle label founded by photographer Adam Brown on the concept of smart men’s swimwear. We also have the likes of Pharrell Williams, LeBron James and Brad Goreski to thank for its comeback.

Will the resurgence of shorts for men be as short-lived as its past revivals, or will it finally become a mainstay in our wardrobe? Only time will tell. But for now, if you are going to incorporate them into your outfits to up your sartorial game, here’s how.

1. The Short Suit

Dolce & Gabbana Spring/Summer 2021 
Photo: Showbit

They key to any suit—even a short suit—is the right fit. Ideally, you’d want to get it tailored or at the very least, altered by to fit you. That said, boxier cuts are on trend for short suits, so you can get away without getting a bespoke piece.

Instead, focus on accessorising. Wearing high socks, like the one worn by the models in Thom Browne’s Spring/Summer 2021 runway, is one way to do it if you’re going for a preppy vibe. If you’re not, ankle-length socks would work just fine. We recommend pairing your suit with chunky sneakers, or leather shoes—but nothing too formal.

If you are going somewhere fancy (an event with a dress code), however, it’s best to leave the short suit home. That said, it’s the perfect outfit for most occasions, especially in Singapore.

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Thom Browne
Classic Backstrap Short In Medium Grey Super 120’s Twill

Klopman Tailored Shorts

Logo Print Shorts

2. Do It With Co-ords

BODE Spring/Summer 2020
Photo: Showbit

Co-ords, also known as coordinating pieces of a set (generally two) are a popular way to wear shorts—especially in the tropics. Generally, the shirts have a revere collar and the shorts are straight-cut or looser. If you’re not big on prints, opt for solid-coloured separates in the same shade to pull off the trend. Alternatively, break up the print with a solid-hued T-shirt or shirt worn under. Layering complementary colours is key here.

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Striped Tailored Wool Shorts

Dries Van Noten
Wide-Leg Floral-Print Satin-Twill Drawstring Shorts

Checked Linen Drawstring Shorts

3. The Elevated Staple

Orlebar Brown, The Dunes Collection
Photo: Courtesy

Tailoring is a quintessential aspect of sophisticated menswear. And it’s what Orlebar Brown offers splendidly through its range of tailored shorts. The silhouette, cut and details in tailored shorts not only elevates your outfit, but it also doesn’t restrict you from having fun.

Whether you’re off to the beach club, a yacht party or simply running errands, pairing a pair of tailored shorts with a T-shirt, polo or lightweight linen shirt is an excellent way to up the ante without much effort. Wear them with your favourite sleek sneakers, or leather slippers and you’re good to go.

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Orlebar Brown
007 For Your Eyes Only Cotton and Linen-Blend Twill Shorts

Stretch Cotton-Twill Shorts

Cotton-Blend Gabardine Shorts