After dating for two years—one spent long-distance between San Francisco and Boston—Thomas Halter Cunningham, senior manager at a 160over90, surprised Jacqueline Rooney, the head of internal strategic response at Meta, with a proposal at ’Sconset Beach on Nantucket. “My engagement ring is especially sentimental—it was my mother-in-law’s engagement ring, and the incredible ladies at M.Flynn in Boston re-set it,” Jackie shares.
Once engaged, Jackie knew exactly where to say, “I do.” “I grew up my whole life going to The Hillsboro Club and always knew I wanted to get married there!” the bride exclaims. “The Hillsboro Club has such a unique old Florida feel, and we wanted our guests to have fun and experience all it has to offer. All four days of events took place at the club, so all they needed to do was show up dressed!”
As for the wedding’s aesthetic, Jackie played on the club’s classic aura and elevated it with a tropical elegance. “I really wanted to play off all the amazing colors around the club and also make every room feel different,” the bride shares. Jackie’s florist, Liz, is a family friend and made her vision come to life. “I wanted to stay away from neutral color palates or traditional wedding flowers [and] have a floral ‘moment’ in each room and orchids EVERYWHERE.” Elizabeth Segilman of Island Life Events and Jonathan Inverso at The Hillsboro Club planned everything and brought warmth to all of the events.
When it came to choosing her wedding weekend wardrobe, Jackie simply states: “I live and breathe by the book of Anny Choi. The end.” The bride enlisted the help of Over The Moon’s head stylist to curate her looks for her engagement party, bridal shower, wedding events, and bridesmaids. She gushes that it was the best decision she made in the planning process. “It was SO collaborative, and it was SO much fun!”
On Friday morning, Jackie wore La Vie Style House x Over The Moon’s white 3d lace maxi caftan, Pascale Monvoisin earrings, and a Porto pouch to her casual bridal luncheon. For the evening’s rehearsal dinner, the bride sported her “something blue,” a custom Markarian dress, with a Roger Vivier clutch. And finally, she changed into a linen Erdem set for the welcome party.
To get ready to walk down the aisle, Jackie wore a Hill House Home dress with Manolo Blahnik shoes. Then the moment arrived for the bride to put on her Carolina Herrera wedding gown, Manolo Blahniks, and rose-adorned veil. The headdress was a small dedication to Jackie’s grandmother, Tillie Rooney, whose favorite flower was a rose. The mother-of-the-bride, Dr. Patrica Rooney, matched Jackie in a bright blue Carolina Herrera dress that the two found during the same appointment when Jackie said yes to her dress. The azul gown “unfortunately was the last one from their resort collection CH had, so Anny helped us special order this for my mom!” the bride shares.
Bridesmaids complemented Jackie well in various dresses that Anny styled and bouquets by Liz McMullen of A New Leaf. “At the last minute Anny suggested custom One/Of by Patricia Voto [fans] for each of my bridesmaids,” the bride says. “They LOVED them and were such a fun addition!”
Halter looked handsome in a Loro Piana blue suit from Knot Standard, a mint-sea foam green tie, Belgian shoes, and a Rolex watch, which Jackie gifted to him.
On May 14, 2022, on the deck overlooking the beach and the lighthouse, Jackie walked down the orchid-lined aisle with her mother to meet Halter at the altar. The bride was 10-minutes early, as clouds were starting to gather and she made the call to start ahead of schedule. “Halter was quite impressed because he is very timely but never thought I would be early,” Jackie laughs. “We squeezed 319 on that deck with additional people viewing from the balcony. I’ll never forget the view looking out to the crowd feeling so supported!”
After exchanging their vows, the newlyweds made sure to get the party started. “Cocktail hour was a blast, especially with my six-foot Hillsboro Lighthouse martini luges and The Hillsboro Club signature drink planters punch out of a fountain,” Jackie shares. “We were at max capacity, so we all ate in the dining room, listening to toasts but then did cake and first dances in The Sea Room next door.”
The new mister and missus had their first dance to “Islands in the Stream” by Dolly Parton and Kenny Rogers. “For my bridal shower, the OTM team gave me this amazing Lingua Franca sweater with the song name monogrammed, and I wear it everywhere,” she gushes.
The bride’s favorite part of the reception was the band, Libido. They had everyone of all ages—even some of the club staff—on the dance floor all night long. After cutting the cake, Jackie changed into her final look of the night—a Naeem Khan dress with Tabitha Simmons shoes. Then a deejay switched it up and played tracks through the early hours. Jackie even reveals, “There might have been a late night pool swim by some of our guests!”
The next morning, the bride said farewells to loved ones in a Coco Shop dress and Rebecca de Ravenel earrings. Later, she and her husband headed to Harbour Island for a tropical mini-moon. The two will be venturing over to Africa for a longer honeymoon over Thanksgiving.
