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The 16th hole of the Port Royal Golf Course

I slam myself back into my seat. Good gracious, I’m thinking, not only do I have to wear shorts, but I have to wear pink shorts? It’s too much for this ankle-skimmer aficionado to handle.

Time for another drink. At 64 Degrees, the bar and restaurant at the Port Royal Golf Course, I’m having a Dark ’n Stormy. This is the national drink of Bermuda, consisting of ginger beer and Gosling’s Black Seal Rum, which is distilled on the island. My view is past the 18th hole, down a sloping green hill and out into the ocean where Bermuda’s ring of coral reefs creates the brightest turquoise water I’ve ever seen. I pull out my research materials on Bermuda shorts and read conflicting accounts on when this fashion fad took over. Some date it to the 1920s, others to after World War II. Either way, the source of the look isn’t in doubt; it’s based on warm-weather British military uniforms, which featured tailored shorts and high socks. This explains why there are stringent rules for wearing Bermuda shorts. The shorts must be tailored, meaning they must be made like typical dress trousers, out of cotton or linen blend. They must have a crease down each leg. They must hit above the knee, with a two-inch hem. Also, they have to be worn with knee socks that are folded down at the top and with dress loafers, a dress shirt, a tie and a blazer or sport coat.

This uniform seems particularly ineffective as shorts go, given that only the very top of the calf and the knee are open to the air. But therein lies its appeal to me: The tailoring of the shorts means I’ll be dressed up when I dress down. Maybe it’s just the Dark ’n Stormys talking, but I’m suddenly convinced I can carry off this look.

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The clock tower at the Royal Naval Dockyard
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A few hours later, Jamahl Simmons deflates my confidence. Simmons, the public-relations director for the Fairmont Southampton, located on the other side of Bermuda from the Fairmont Hamilton Princess, tells me the time for Bermuda shorts as a fashion trend may be running short. “The shorts are something that my grandfather wears,” explains Simmons, a baritone-voiced Bermuda native with the frame of a Division II defensive lineman. “It’s a look for the older generation.”

Even so, Bermuda’s English Sports Shop, the main retailer of Bermuda shorts on the island, still sells about 20,000 pairs a year. Some of those go to conventioneers and visiting businessmen, others to local executives. But Simmons isn’t alone in the belief that fewer men are wearing the Bermuda shorts uniform to work than in years past. As this island nation’s workplaces have followed the worldwide trend toward ?more-casual dress, the demand for the dressy Bermuda shorts has waned. Air-conditioned offices haven’t helped, either. (Who wants cold knees at work?)

Today, the biggest buyers of Bermuda shorts seem to be people like Simmons and Griffith — those who interact daily with tourists. The Fairmont, like other hotels here, requires its male employees to wear the traditional dress during the warm season, which, during my visit, was just days away. And the women in Simmons’ office were counting down the days to shorts season. “They have been torturing me for two weeks,” Simmons says. “They keep telling me, ‘Hey, I want to get a look at those legs.’

“Man,” he continues, breaking into a powerful laugh, “I feel objectified.”

Today is the day. After one more morning? of touring the island’s sites — from the Royal Naval Dockyard in the west to the eastern town of St. George’s, which ?celebrates its 400th year of continual settlement this year — I’m preparing to don Bermuda shorts. I head to the English Sports Shop on Front Street, where I find dozens of pairs arranged in appropriately tidy piles. Here, too, are the must-have knee socks and preppy ties and shirts and blazers. But there is one problem. “We don’t have our spring colors in stock yet,” says Jackie, the sales clerk who is helping me. “Just the gray and navy and khaki.” Having dodged the pastel-colored bullet, I go with gray.