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Shelter Island: Where the Fashion Set Actually Go to Unwind

The coolest of the cool crowd are abandoning the South Fork for this quieter spot.

The last time I went to Montauk, I was so stressed out about going to a luxury brand's Saturday night event that I didn't really enjoy the home my friend had rented for the summer. I didn't really enjoy the smoked whitefish salad that I inhaled between swims in her private pool. I didn't really enjoy any of it because I felt like I was at work.

And that's the terrible thing about the Hamptons, and now Montauk: They're totally fun for a night or two, especially if you're out there for a work event. But if you're there to unwind, like I was, and you have trouble unwinding, like I do, they're just not very relaxing.

Enter Shelter Island, the chunk of land right smack between the North and South Forks of Long Island, which, if our Instagram feeds are any indication, has become something of a hotspot for the fashion set. For those aiming to avoid the throngs of partiers in the Hamptons and Montauk, but want to stay somewhere a bit more glam than the North Fork—which is awesome, but not fancy at all—Shelter Island provides a nice balance. "I think certain areas around Shelter Island have grown too big for some peoples' tastes," says Steven Jauffrineau, who's in his fourth season as general manager at André Balazs' Sunset Beach, a luxury boutique hotel on the island. (Leah interviewed him last week on a trip to see the property.) "We're definitely seeing more traffic this year than we have in the last few years." The result is better, hipper services. For instance, Sunset Beach has updated its menu to keep up with the palate demands of a newly discerning audience. "As more people choose Shelter Island as their vacation home of choice, and the money pours in, overall service is elevated—the food and fashion is better because we have a much more well-traveled guest."

Jen Mankins, the owner of Brooklyn's Bird boutiques, has been spending summers with friends and family on Shelter Island for more than a decade. This season, she decided to bring Bird with her, opening a seasonal pop-up. "I've been thinking about doing a small beach store for the past few years and this spring there just happened to be the cutest, most perfect little spot available right on the water in the middle of town," she says. "It never occurred to me not to do it on Shelter Island. I feel such a connection to the people and the place, it just felt right."

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Of course, not everyone is thrilled with the idea of Shelter Island becoming a thing. One prominent fashion insider we reached out to—who, mind you, consistently posts photos of Shelter Island on his/her public Instagram declaring how great it is—declined to comment for this story for fear that it might draw too much attention to the under-the-radar getaway.

Well, our Instagram friend might be safe—for now. Both Mankins and Jauffrineau are skeptical that crazy partiers are about to overtake their little piece of heaven. "Having ferries [as the only way to get there] really helps control the crowd," Jauffrineau says. Adds Mankins, "The island is so sleepy and really just about friends and families going to the beach and making big dinners. So I really don't see it becoming too crazy anytime soon."