Brooklyn in the Catskills
Adidas slides, $34.99 at Foot Locker, footlocker.com; Lisa Marie Fernandez bonded stretch-nylon swimsuit, $370 at net-a-porter.com; Alexander Wang mesh and knit pullover, $595 at Nordstrom, nordstrom.com; Topshop high-waist denim shorts, $58 at Topshop, topshop.com.
St.-Tropez on Shelter Island
Jade Swim stretch-nylon swimsuit, $198 at Matches, matchesfashion.com; Missoni Mare lace-up caftan, $679 (on sale) at modaoperandi.com; J. Crew beaded tassel earrings, $65 at J. Crew, jcrew.com; K. Jacques wedge sandals, $325 at Ann Mashburn, annmashburn.com.
Americana in Montauk
Solid & Striped retro gingham swimsuit, $170 at matchesfashion.com; Ace & Jig cotton madras jumpsuit, $340 at Bird, birdbrooklyn.com; woven straw basket, $68 at Free People, freepeople.com; Castaner denim wedge espadrilles, $155 at Intermix, intermixonline.com.