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What to Wear: Natty in Nantucket

What was once a quaint whaling village in the 1800s, Nantucket has emerged as a posh vacation enclave. On humid August weekends, New Yorkers and Bostonians flock to the charming shingled cottages and breezy white sand beaches. And with such easy proximity to Northeast cultural centers, Nantucket has a certain polish not always found in seaside locales. Well-known politicians, artists, writers, and media personalities, from Herman Melville to Katie Couric, have vacationed here. So while this may be the seaside, you should dress to impress. Here are some of our top picks for your ideal weekend wardrobe.


While the Sun Is Still Shining


All-American classics with a WASPy twist are the usual mode here. For daytime, anything Ralph Lauren is safe. Rather than going for in-your-face polo ponys, we like this v-neck sweater in a classic orange ($101, was $198) with subtle matching stitch logo. The color will transition well into fall with dark denim or navy cords. But while the summer sunshine is still out, slip the sweater over a Liberty floral button-down shirt ($150)—we were inspired by the heath covered moorings on the island—and get the last wears out of your white chino shorts ($29.99, was $40).

Pull the outfit together with neutral accessories, perked up with texture and new materials. For one, these eco sunglasses by Panda ($158) are made of sustainable bamboo, and with each purchase the company will provide an eye exam and prescription glasses for someone in need. (Take that, buyer’s remorse.) And when picking a belt, stick with a traditional braided cincher for versatility. Gap has a slim, feminine version ($19.95) that will go well looped through shorts and over dresses. This late into the season, new sandals should be sensible rather than trendy. This calfskin version by Ancient Greek Sandals ($255) with lacing details are handmade in Greece and have a secure ankle strap for strolling in harbor villages. (Michelle Williams was recently spotted wearing the same shoe in a darker shade—bonus points.) A canvas tote works well for beach essentials, but for a dressier daytime affair, this heritage design by Coach, aptly called the Legacy duffle, stands out in a bright sea blue ($348).

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When the crowd is of the more buttoned-up sort, real pearl studs, a more casual interpretation of the usual pearl necklace, are a good solution ($30). They’ll dress up this day-or-night madras sundress ($54.95, was $64.95). On footwear, pick a wedge that can go from the restaurant to after-dinner drinks on the lawn. With the end of summer near, many, like this Chloe version with pretty tricot edging and cut-outs, are on sale ($334, was $476.63). Lastly, tap into the country atmosphere by pulling it all together with this wicker box clutch ($275 by Tory Burch).


Sailing Weather


With Nantucket’s whaling history, a “ship’s ahoy” culture resonates in daywear. If you’re brave enough to fully embrace New England prep, pull on a pair of shorts with embroidered fish or whales. Didn’t bring your own? Stop into Murray’s Toggery Shop at 62 Main Street to snag this sun-faded coral pair dabbled with bluefish ($98), an ode to the plentiful local species. To avoid looking too in-costume, keep it simple up top with slim v-neck tees in white and gray ($24.50 each from Banana Republic). If your activities tend to be more formal, choose a polo with extra oomph like the ribbon trim on this Michael Kors edition ($125).

Add fashionable accents from American heritage brands like Persol. These dark brown frames ($360), with the brand’s identifiable nose bridge notch detail, are a handsome evergreen. And even if you’re not actually going sailing, you can take the sport as a general wardrobe guideline. These canvas sneakers by Generic Surplus ($57.99, were $72) have lacing inspired by traditional boat shoes.



With salty ocean breezes that pick up in the evening, Nantucket is an ideal spot to try out fall’s new pieces. Navy paired with aubergine looks fresh for the cooler months ahead. Wear together, as in this dark blue cotton-cashmere cardigan ($49.95 by L.L. Bean) and plum chinos ($180 by Reiss) combo. On the weekends, trousers can be belted (this bright blue canvas and leather option is now a steal at $10.40 a pop, originally $26 each), then cuffed and rolled just above the ankle. The styling point will be all the better to show off a great pair of kicks like these suede tassel loafers by Mark McNairy ($395 at Club Monaco) worn sockless (or with low-profile loafer socks) of course. The bright yellow outsoles give a good dose of quirky fun. And sometimes, simplicity is best for true all-American style; this minimal Braun black leather strap watch with stark white dial ($210 at Steven Alan) stands out confidently above the rest.

What to Do

Sailing enthusiasts will revel in the spirit of the island’s annual Race Week. Kicking off this year on August 11 and going until August 19, expect regattas, parties, and award ceremonies. And because this is luxurious Nantucket, the race’s accompanying raffle prizes include a Panerai watch and diamond bracelet.

Novices can get their hands wet by taking a lesson through the Nantucket Community Sailing organization that offers classes for ages 5 on up. A few more programs are available through August, or you can always book a private session.

Land-lubbers also have plenty to see. Rent a bike at Young’s Bicycle Shop (they also rent out cars and jeeps) and pedal the popular but no less scenic route to ‘Sconset. (Grab a fantastic and hugely portioned sandwich to go at Something Natural before you depart.) The 8.2 mile loop over Milestone and Polpis roads will also take you past Sesachacha salt pond, which is brimming with clams and fish. The area is also home to the Audobon Heathlands Wildlife Santuary making for excellent bird-watching.

Photo Credits: Women: Top left, Anthropologie; Bottom left, Coach, Inc.; Left center,; Bottom center, J.Crew; Right center, J.Crew; Top right, Gap Inc.; Bottom right,; Left, Gap, Inc.; Center,; Top right, Neiman Marcus; Right, Men: Top left,; Bottom left,; Center, Michael Kors; Top right, Murray’s Toggery Shop; Bottom right,; Left, Reiss; Bottom left, Kohl’s Illinois, Inc.; Center, Steven Alan Holdings, LLC.; Top right, L.L.Bean Inc.; Bottom right, Club Monaco US, LLC

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