New Yorkers are funny creatures. Even when leaving the confines of the city, they tend to gravitate to the same sorts of places they frequent at home. Those with a taste for classic luxury — who wouldn’t look out of place on a vintage sailboat — can be found recharging beachside at a well-known hotel and spa like Gurney’s Montauk. Those who pride themselves on going off the beaten path (and may or may not live in Brooklyn) will flock to Graham and Co., a converted motel in the Catskills that gives complimentary Budweiser upon arrival. Fans of the party atmosphere and glamorous crowds particular to André Balazs properties will be popping bottles at Sunset Beach, his Shelter Island spot. Needless to say, whichever camp you happen to fall into, you have to dress the part.

CreditPoul Ober

Brooklyn in the Catskills

For some New Yorkers, leaving the city does not necessarily mean leaving the street’s influence behind. Black denim cutoffs and a checkerboard Alexander Wang pullover retain an urban edge even in the great outdoors. And, when paired with a sporty swimsuit and easy slides, they’re ready for poolside lounging or fireside cuddling on Graham & Co.’s laid-back grounds in Phoenicia, N.Y.

Adidas slides, $34.99 at Foot Locker,; Lisa Marie Fernandez bonded stretch-nylon swimsuit, $370 at; Alexander Wang mesh and knit pullover, $595 at Nordstrom,; Topshop high-waist denim shorts, $58 at Topshop,

CreditSunset Beach

St.-Tropez on Shelter Island

At Sunset Beach in Shelter Island, N.Y., there is never a shortage of people-watching or frosé, the hotel’s popular frozen rosé. A crochet Missoni caftan worn over a plunging one-piece allows you to take in the scene while soaking up the sun — preferably with drink in hand. Statement earrings and simple wedges keep the look suitably glam for the setting.

Jade Swim stretch-nylon swimsuit, $198 at Matches,; Missoni Mare lace-up caftan, $679 (on sale) at; J. Crew beaded tassel earrings, $65 at J. Crew,; K. Jacques wedge sandals, $325 at Ann Mashburn,

CreditGurney’s Montauk

Americana in Montauk

The Hamptons’ only beachfront restaurant and bar — the yellow-and-white-stripe-bedecked Beach Club at Gurney’s Montauk — calls for classic Americana. And what’s more classic than pastel madras? Ace & Jig’s breezy cotton jumpsuit nails that sweet spot between retro and right now. A circular straw bag and beach-worthy espadrilles rounds out the look.