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St. George’s Island
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I need a drink. Some liquid resolve that might help convince me to, at some point in my stay, put on shorts in public for the first time since I was a kid. So, still dressed up, I head to the Fairmont Hamilton’s Friday happy hour. Friday happy hours are a big deal on this island, possibly because most people here need to unwind after a week’s work in the complex financial industries that dominate the island’s economy — re-insurance and offshore tax shelters. Every year, millions of dollars pass through a network of businesses that have only the faintest presence in Bermuda. How faint? Some 15,000 companies are registered to do business on this 21-square-mile island of 65,300 people.  But, of course, there’s real money to be made passing around all those millions, and as a result, Bermuda has the fourth-highest per capita income in the world, trailing only Liechtenstein, Qatar and Luxembourg, according to the CIA World Factbook. This is just one of the things that set Bermuda apart from its Caribbean counterparts 1,000 miles to the south.

The clothes are another. At the Friday happy hour, I’m not the best-dressed person. Not even close. That honor goes to William C. Griffith, Bermuda’s director of tourism. He breezes through the happy hour before I join him for dinner at the Fairmont’s Heritage Court bar and restaurant, just off to the right of where Mark Twain sits. Griffith is clad in a pinstripe navy suit and a purple shirt and tie. He’s accessorized with a large, shiny gold watch, a dangly gold bracelet and black eyeglasses that have gold strips on either side.

I tell Griffith, on this day in early April, that I expected him to be wearing Bermuda shorts. “Oh, no,” he says with a Jamaica-meets-Scotland accent that’s typical for Bermuda. “It’s too cold now. Two more weeks and I’ll wear them.”

He’s right. The day we meet, the high is in the low 60s. The weather is another thing that makes Bermuda different from the Caribbean. Summers are mild, not sweltering, and winters can get a bit chilly. This is good news for me. It means that Bermuda shorts season is, well, short. And indeed, so far I’ve only seen one person on the island wearing the national dress. I’m thinking: Maybe I don’t have to wear shorts after all.
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Locals sporting the native dress
Doug Wilson/Corbis

Wandering around the next afternoon, I am further encouraged to abandon my plan to dress like a local. Plenty of businessmen who work on and around Front Street, the main artery in downtown Hamilton, the tiny nation’s capital, wear Bermuda shorts. But I see none. Then I remember: It’s Saturday, stupid. No one is working.

A little later on, I’m still shorts-spotting while riding in the back of a taxi headed west on Bermuda’s South Road. On one side of the street, perfectly kept homes flutter by like wildly colored flags. Aquamarine, pink, lavender, peach and all other imaginable shades of primly painted pastels, the houses sit on lawns landscaped almost as perfectly as the eight golf courses that are wedged into every corner of the island. Bermuda is all about wedging. If it were an independent country and not a British protectorate, Bermuda would be the third-densest nation on the planet, with 3,000 people per square mile. That’s one of the reasons visitors aren’t allowed to rent cars here — only scooters — and the primary reason Bermudians can only sell their homes to other Bermudians, who, last year, paid an average price of $1.2 million for one.

As our taxi ride continues, I spot Elbow Beach, one of the most popular and biggest pink-sand beaches on Bermuda. There, I finally see men in shorts. Cargo shorts. Bulky, brown, ridiculous cargo shorts. To some they must be comfortable. But not to my eyes. Cargo shorts, to me, make grown men appear like overgrown children. I lean up to the front seat to ask Joy Sticca, the communications coordinator for Bermuda’s tourism department, what she thinks of the island’s trademark fashion. “I think the men look sexy in those shorts,” she says. “I like the colors too. The pink is nice.”