1. Real Weddings

An Elegant Wedding at Ram's Head Inn in Shelter Island Heights, New York

Jenna Hershey (27 and a fashion publicist) and JP Covello (31 and a hedge fund trader) planned an elegant, relaxed soiree for their early-fall wedding

Jenna Hershey (27 and a fashion publicist) and JP Covello (31 and a hedge fund trader) planned an elegant, relaxed soiree for their early-fall wedding in Shelter Island, New York. “Shelter Island is a really meaningful place for us and our families,” Jenna says. “Ram’s Head Inn is minutes away from my family summer home and has the most beautiful, quintessentially Shelter Island setting—on a hill just past the Ram Island causeway, overlooking Coecles Harbor.” Since they wanted the event to embody the island's carefree feel, Jenna and JP chose a soft palette of gray, green, flax and off-white and filled the day with rustic, coastal touches, such as seashells, farm tables, a Sperry tent and garlands of lush greenery and fresh white florals. The ceremony took place outdoors overlooking the harbor, where Jenna and JP exchanged vows under a white birch wedding arch adorned with ethereal white fabric and silver dollar eucalyptus for a bohemian look. “We didn’t want anything to take away from the view,” Jenna says. After making their exit to the Beatles’ “Here Comes the Sun,” Jenna and JP joined their guests for cocktail hour. The newlyweds served Aperol Spritz and Spiked Watermelon Agua Fresca alongside rustic platters of cheese, meats, crudit?s, mini lobster rolls, fish tacos and pork sliders, much to the delight of guests. Live acoustic renditions of the Beach Boys, reggae and other beach tunes filled the air, setting a relaxed tone. Dinner ensued under a sailcloth tent. “It was important to us to create an intimate space that felt like a dinner party at home,”  Jenna says. Guests gathered around long farm tables draped in gray linen tablecloths and bathed in warm candlelight. Long, lush garlands of silver dollar and seeded eucalyptus dotted with dahlias, ranunculus, garden roses and snowberries injected the tablescapes with a whimsical, garden-inspired flair, while vine-covered chandeliers and strands of bistro lights cast an ambient glow over the dance floor. When guests had gotten their fill of succulent, seasonal eats, they headed indoors to get their groove on. The mellow string trio gave way to Play Something Good, which churned out high-energy hits all night. A tip from Jenna: “Enjoy being engaged, and stay present throughout the planning process—it’s easy to get lost in all the details. Make every decision based on what’s important to you and your fiance. And stay with each other all night—holding hands helps!” —Libby MacCarthy

With the majority of her jewelry box featuring yellow and rose gold pieces, Jenna selected a rose gold pave ring for her wedding band. JP followed suit to complement Jenna’s style, choosing a solid rose gold band that was both timeless and modern.
The escorts struck the ultimate balance of sophistication and pastoral charm, with calligraphed gray cards displayed atop a bed of fresh green moss and snowberries laid neatly in wooden trays.
“I had a vision for my bridesmaids to wear long, breezy dresses in soft gray to echo the gray-blue skies and often windy weather on Shelter Island,” Jenna says. While Jenna and her ladies originally had their sights set on nonbridesmaid dresses, they ultimately walked down the aisle in dove gray chiffon gowns by Amsale, each girl wearing a style of her choosing.
Sag Harbor Florists infused Jenna's and the bridesmaid bouquets with a fresh, just-picked feel, creating loose, romantic arrangements of ranunculus, garden roses and cafe au lait dahlias offset by cascades of silver dollar eucalyptus.
While JP opted for a modern navy Shawl collar tuxedo from J.Crew, his groomsmen donned traditional black styles, which they rented from The Black Tux. They completed the look with black suspenders, bow ties and patent dress shoes.
The ceremony took place outdoors overlooking the calm waters of Coecles Harbor, where Jenna and JP exchanged vows under a white birch wedding arch adorned with ethereal white fabric and silver dollar eucalyptus for a bohemian look. “The ceremony overlooked Cockles Harbor, and we didn’t want anything to take away from the view,” Jenna says.
The couple gathered their family at Ram’s Head Inn in Shelter Island Heights, New York, for an intimate rustic soiree with endless elegant appeal. “Shelter Island is a really meaningful place for us and our families. Ram’s Head Inn is minutes from my family's summer home and has the most beautiful, quintessentially Shelter Island setting—on a hill just past the Ram Island causeway, overlooking Coecles Harbor,” Jenna says. As guests arrived to the fete, they passed under a striking garland of greenery and full white blooms.
In lieu of favors, Jenna and JP gave their guests welcome bags upon arrival. The kits were filled with a spread of local treats, including mini bottles of Wolffer Estate Rose Cider, North Fork Potato Chips, Tate’s Chocolate Chip cookies and more. A hand-drawn map of the island and the weekend itinerary were also placed inside each pack, giving guests the lowdown on the locale and all the wedding’s fun-filled festivities.
Wooden country chairs with crisscrossed backs lined the long reception tables, lending a hint of Provencal elegance to the expansive open-air tent.
“In the tent, it was important to us to create an intimate space that felt like a dinner party at home,” Jenna says. Four long tables ran the length of the tent, draped in gray linen tablecloths and verdant garlands of silver dollar eucalyptus, dahlias, ranunculus and garden roses. Candlelight, bistro lights and vine-covered chandeliers bathed the tent at Ram's Head Inn in Shelter Island Heights, New York, in warm, ambient light.
The cocktail hour menu featured Jenna and JP’s favorite libations—Spiked Watermelon Agua Fresca and Aperol Spritz—offering a refreshing way to kick off the evening’s festivities. The signature sips were served alongside rustic platters of cheese, meat, crudités, mini lobster rolls, fish tacos and pork sliders, much to the delight of guests. Live acoustic renditions of the Beach Boys, reggae and other beach tunes filled the air, setting a relaxed tone for the evening.
In lieu of traditional place cards, Jenna and JP had guests' names letterpressed onto the menu cards. Featuring ivory card stock and soft gray script, the menus matched the tables’ refined gray linens.
After a dinner of Montauk striped sea bass with corn succotash and crispy local kale, guests indulged in a selection of Briermere Farms fruit pies and coconut cake from Sag Harbor Baking Co. Garlands of fresh greenery adorned the two-tier confection, playing up its bohemian flair and tying to the scenery at Ram's Head Inn in Shelter Island Heights, New York.