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Dressing by Destination: What to Wear in the Top 5 Summer Vacation Spots

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    Photo: Alamy
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    Positano, Italy

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    Photos, clockwise from top left: Courtesy of farfetch.com; Courtesy of ivisionari.com; Courtesy of dolcegabbana.com; Courtesy of net-a-porter.com; Courtesy of 1stdibs.com
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    Vivetta layered T-shirt, $357, farfetch.com; Kaleos Caster sunglasses, $180, ivisionari.com; Dolce & Gabbana printed bikini with triangle bikini top, $545, dolcegabbana.com; Castañer Carina canvas wedge espadrilles, $110, net-a-porter.com; Emilio Pucci circa 1960s pink and orange floral miniskirt, $674, 1stdibs.com

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    Photo: Alamy
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    Montauk, New York

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    Photos, clockwise from top left: Courtesy of modaoperandi.com; Courtesy of farfetch.com; Courtesy of luisaviaroma.com; Courtesy of llbean.com; Courtesy of barneys.com
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    Gül Hürgel polka-print peplum midi dress, $795, modaoperandi.com; Stella McCartney cat-eye-frame sunglasses, $345, farfetch.com; Alex Pagoda wide-brim straw hat, $202, luisaviaroma.com; L.L. Bean open-top Boat and Tote, $25, llbean.com; Tabitha Simmons Virginia leather ankle-strap sandals, $625, barneys.com

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    Photo: Alamy
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    Cape Town, South Africa

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    Photos, clockwise from top left: Courtesy of staud.clothing.com; Courtesy of armynavydeals.com; Courtesy of farfetch.com; Courtesy of sephora.com; Courtesy of needsupply.com
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    Staud Mongo jumpsuit, $205, staud.clothing; Uncle Sam’s khaki military boonie hat, $20, armynavydeals.com; Gucci Flora print neck bow, $185, farfetch.com; Fresh Sugar Sport Treatment Sunscreen, $25, sephora.com; Martiniano glove shoes in coral, $437, needsupply.com

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    Photo: Alamy
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    Cartagena, Colombia

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    Photos, clockwise from top left: Courtesy of matchesfashion.com; Courtesy of avenue32.com; Courtesy of fwrd.com; Courtesy of shopbop.com (2)
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    Pippa Holt No.72 embroidered cotton caftan, $918, matchesfashion.com; Ranjana Khan multi pom-pom clip-on earrings, $440, avenue32.com; Rag & Bone Calla braided belt, $195, fwrd.com; Nannacay Joana multi medium tote, $260, shopbop.com; Ancient Greek Sandals Eleftheria sandals, $250, shopbop.com

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    Photo: Alamy
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    Bangkok, Thailand

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    Photos, clockwise from top left: Courtesy of realisationpar.com; Courtesy of avenue32.com; Courtesy of farfetch.com; Courtesy of fernfans.com; Courtesy of matchesfashion.com
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    Réalisation Par The Emilie Shanghai Nights dress, $160, realisationpar.com; Annie Costello Brown gold-cube chandelier earrings, $265, avenue32.com; Vince Compact T-shirt, $107, farfetch.com; Fern striped fan in blush pink, $78, fernfans.com; Gucci Hannelore detachable-platform velvet pumps, $1,890, matchesfashion.com