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What to Wear: Weekend in Bermuda

Over the years, and with the help of a Beach Boys tune, Bermuda has earned a reputation for romance and beautiful pink beaches. But contrary to some other island retreats, it has generally avoided the pitfalls of giant megaresorts and uninspired tourism, thanks in large part to its affluent population. Instead, with British ties as an overseas territory, Bermuda exudes a certain posh-ness. Here we have some key pieces to add pep (and a touch of prep) to your vacation wardrobe.

Women: Elegant Classics


Far from the wild, bohemian habits of say, Ibiza, Bermudians favor clean, elegant silhouettes with a hint of prep school. Start with the namesake Bermuda shorts in twill ($36.95 at American Eagle). The longer length can be tricky, so pay attention to proportions. Go for a slimmer style and wear with a loose breezy top—this peachy mesh-silk combo tee by Alexander Wang ($164) feels right with a tan under the shimmering island sun—and sleek T-bar sandals ($29.99 by Nine West). For trips to the tennis club or the beach, a beach tote that doubles as a sturdy carry-on will do the trick. Luggage company T. Anthony, a favorite of Jackie O., is a good option. The company offers a lifetime warranty on all its wares, making this mainstay, the Town and Country tote, worth its price ($325). If your day includes cruising along South Road with your convertible top down, then tying on an Hermes silk scarf ($410) is a tried-and-true glamorous touch. Pair with movie star shades ($128 by Kate Spade) and you might just turn a few heads.

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At night, the island breezes kick up, so bring a jacket or light sweater. Nod to the isle’s pink beaches, made from seashells, with a bright jolt of pink cashmere ($188 by J. Crew). Leave the neutrals to your dress; a cream and black printed frock makes for easy pairing ($209.30 by Jill Stuart). A smart way to save a few dollars on accessories is to look for pieces from museum stores—Alexis Bittar, for example, was first carried by the Guggenheim museum. This mother-of-pearl clutch from the Smithsonian is a steal at $30. Finish with wooden platform heels ($39.99), a reference to the island’s rattan furnishings.

Men: Sport and Sun


Though London may be the star of the summer, those looking for Brit flavor without braving Heathrow will find the culture alive and well in Hamilton, the capital of the British overseas territory. During the day, poke fun at the mystical "Bermuda Triangle" with a bit of T-shirt satire. ($34 at Barneys for a triangle print tee). On bottom, go for simple swim trunks in a cheerful pink, like these by cool Atlanta-based shop Sid Mashburn ($75). Canvas boat shoes ($46 by Tretorn), also great for wearing on the plane, round out the outfit. They can go swiftly from beach to deep-sea fishing. And while the sea spray is splashing, snag a preppy case for your iPad. Splendid has a striking collaboration with accessories designer Claire Vivier ($128), whose striped pattern will contrast nicely with Filson’s rough and tumble water repellent tote bag ($90).


At night, rugby fanatics will have much to cheer about. Along with football (er, soccer), rugby is big in Bermuda. Snag a polo, inspired by the sport, before touching down ($54.99 by Rugby). Wear with these versatile reversible shorts with micro-stripe on one side and cheerful gingham on the other ($68.95 in breathable cotton by Life After Denim). Really feeling the WASP-y vibe? Throw a New England-style patchwork belt into the mix ($39.50). But if that’s bordering on prep overdose, reel back a bit with these masculine John Varvatos slip-on sneakers ($112.50) in suede and leather. Lastly, in a nod to British dandyism, skip the cologne in favor of men’s fragrant oil ($22). The rose, carnation, and musk scent will have you feeling island in no time.

What to Do

Bermuda, with its position in the Atlantic, generally has a milder hurricane season (June to November) than the Caribbean isles. Still, if you’re going this time of year, be ready for periods of rain. In September, the island will be celebrating John Lennon and his music. In 1980, the Beatle famously visited the territory, which provided a flurry of inspiration, by sailing from Newport on stormy seas. Local artists and musicians will be paying tribute with a special concert on Sept. 21 at 8 pm at the Botanical Gardens. To listen to songs for the tribute in advance, check out:

Speaking of rugby, Bermuda hosts the World Rugby Classic every year. The weeklong event means plenty of parties and live music post-match. Coconut Rock is a great spot to chat up a local on the game.

Events aside, Bermuda’s pristine beaches are the main draw. Head out to Horseshoe Bay for snorkeling, swimming, and sunbathing. The 4-mile stretch can get crowded, however, especially when cruise ships are in port, which is when you should hightail it to Jobson’s Cove Beach, especially good for kids, or Church Bay Beach for world-class snorkeling.

Want more tips on what to wear on your next holiday? Check out What to Wear: Honeymoon Edition, What to Wear in Montreal, and What to Wear: Surf Style in Santa Cruz.

Thinking of a trip to Bermuda?

For up-to-the-minute hotel and restaurant recommendations, as well as the best planning advice, check out our Bermuda Travel Guide.

Photo credits: Women: Top left, Hermes; Bottom left, T. Anthony; Top center, Alexander Wang, Inc.; Bottom center, Gap Inc.; Top right, Kate Spade; Bottom right, AEO Management Co.; Left,; Center, J.Crew; Bottom center, Smithsonian Institution; Bottom right, Zara. Men: Top left, Splendid; Bottom left, Sid Mashburn; Center, Barneys New York; Top right, Timothy Aguero Photography/C.C. Filson Company; Bottom right, PUMA North America, Inc; Top right,; Bottom right, John Varvatos; Center, STAG; Right, Ralph Lauren Media LLC; Bottom right, Hollander & Lexer

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