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Shorts and socks? Only in Bermuda.


The deck of the 100-foot yacht Venetian erupts in cheers and a flurry of fluttering union jacks as the British ship, Land Rover BAR’s carbon fibre catamaran “Rita”, whips across the finish line. This year the white sand beaches and turquoise waters of Bermuda’s Great Sound are home to the 35th America’s Cup, sailing’s foremost prize. As a gathering of billionaires, Olympic sailors and the global yachting set, it also happens to be the perfect setting to observe nautical style in its natural habitat.


The first thing one notices on the deck of a yacht in Bermuda is that, yes, Bermuda shorts are indeed a thing. While this odd mix of business and holiday—button down shirt, short shorts, loafers and black socks pulled up to the knee—is entirely appropriate attire for Bermudans, it’s not particularly flattering. A Canadian man in search of a perfect nautical look should certainly embrace the above-the-knee shorts, but ditch the high socks in favour of a more relaxed, Mediterranean aesthetic. Instead of boat shoes, a pair of espadrilles or waterproof slip-ons will carry you from the boat to the bar in style.

Linen abounds among the nautical set, and for good reason. A scorching summer day demands clothing that will keep you cool, something linen’s light, loose weave does with aplomb. A linen shirt in a bold print, paired with a light-coloured sport jacket and shorts will do the trick. While wrinkles and a relaxed fit are a natural part of this summer staple, a tailored fit is still important to avoid looking rumpled.

Oddly enough, one thing one doesn’t see on deck at the regatta is that classic of nautical dressing, the horizontal blue-and-white Breton stripe. Perhaps too on-the-nose for wear onboard a yacht, a timeless striped tee or light sweater is the ultimate statement of seafaring nonchalance and entirely appropriate for any casual summertime occasion. Pair with a navy blue blazer and lightweight denim jeans for the ideal mix of surf and turf.