The date for the couple’s town hall wedding was set for September 6—a sweet nod to Samantha’s parents’ anniversary, which is the reverse numerically, June 9. They landed on a carnival concept for the wedding itself, with an arcade room, games, and prizes. “We wanted our guests to discover new things at every turn, so that there was always a surprise and delight element,” Samantha says. The invitations—designed by Cheree Berry—featured a pinwheel graphic, which became the foundation of all the creative elements of the wedding.
The weekend began with a bridal lunch hosted by Will’s mother and sisters at Galley Beach, one of Samantha’s father’s favorite restaurants, with a clam bake held later that evening for close friends and family. The Friday was just as busy, with the town hall ceremony in the morning, followed by a rehearsal dinner at Ventuno in the evening. “We had the whole second floor, and it felt like we were all at someone’s house,” Samantha describes. “Lucky for us, we had Tyler whipping up his famous espresso martinis!” Everyone then moved on to the welcome drinks, which took place at Cru. “So many of our guests had never been to Nantucket before, and there is no better place to show off the beautiful harbor.”
Samantha has always been a fan of archival fashion, so she decided to go fully down the vintage route for her wedding. After managing to bag an appointment with Alexis Novak from Tab Vintage (“My stylist friend Marni Senofonte managed to get me a slot!”), she asked her to do all her wedding looks. “Alexis is so insanely talented and has the most incredible eye,” she shares. “I feel beyond lucky she agreed to work with me.”
For her ceremony outfit, she settled on the 1991 cut-and-slash Vivienne Westwood gown. “It was so visually interesting and a bit rebellious,” Samantha says. “I kept warning people that this was not a normal wedding dress. But every time I tried it on, I would get so excited—it had this energy that was really special.”
After finding that first dress, Samantha and Alexis kept discovering more looks that they liked. “I couldn’t stop myself,” laughs Samantha. “I just kept slotting in events so I could wear another look!” During a trip to London’s One Of A Kind Archive, Samantha and her mother found a Thierry Mugler suit and a crochet Chanel dress. “When I saw that suit, with the shell-like pattern, I was smitten,” she explains. “It felt so modern, yet gave a nod to our island wedding. The Chanel dress had this crochet train that felt very Nantucket—it felt like kismet to find these two pieces in that incredible store, and it brought back special memories for my mom and me, who 20 years ago combed through their archives to find bat mitzvah dresses.” Other major fashion moments included a 1992 Chanel dress and jacket, which she wore for her town hall ceremony, and a 1999 Christian Dior mini and 1994 Versace dress, which she wore for her bridal lunch and the clam bake respectively.