The Bride Wore All Vintage to Her Wedding at a Gilded Age Mansion in Newport

Growing up in New York City, actress Caroline Margaret Day and film executive Samson Day had been in the same room—at the same party or concert—probably a dozen times without knowing it. But they didn’t actually meet until freshman year of college, when they were set up by one of Caroline’s friends. “On our first date, we walked around Manhattan and snuck into a movie theater in Union Square for a late-night showing,” Caroline remembers. “We were 18—just kids—so all of our early dates were so sweet and innocent. We can’t walk around the city now without remembering something we did together in those early days—going to Mr. Softee, riding bikes on the West Side Highway, driving through the snowbanks when the city was shut down during a blizzard. In a way, we grew up together, which was not something we ever planned or imagined for our lives, but makes us feel like the luckiest people in the world.”
The summer after they graduated from college, they decided to take their young love abroad and travel through Europe together. “I had chopped my hair into a bob and packed super casually, and I found it very odd that Samson kept insisting that I get my nails done,” Caroline remembers. “This would have been my only clue, but it went right over my head.” They were on the train from Paris to London when Caroline’s agent called her with an audition, and she had only a few hours to prepare. Thankfully, the character was described as wearing “a floral dress and red lipstick,” and even though she didn’t have much with her, she had a floral dress, and she always carries red lipstick. “In my haste to finish [getting ready for] my audition in time, I didn’t even think about the fact that I was wearing one of Samson’s favorite of my dresses, and that he always loves when I wear red lipstick. He had gotten us the sweetest room in London, with a big claw-foot tub and a view of the city, and he quickly set up the camera to do a [practice] tape. Once we started rolling, he got down on one knee and proposed—and it was all caught on camera. Samson had written a scene that incorporated people and places from our relationship disguised by anagrams and riddles. He asked my agent to go along with it. She kindly obliged. Afterward, we walked along the Thames and marveled at all of the coincidences and missteps and perfect circumstances that led us to be together forever.”
Caroline and Samson knew they wanted to get married in Rhode Island, as it was a convenient location for both of their families. When they walked into the Rosecliff Mansion, an estate that actually served as one of the shooting locations for the 1973 adaptation of The Great Gatsby, they couldn’t picture a more perfect place.
They decided that the venue should inform all of their stylistic decisions, and created a simple mood board with just a few references for their planner, Serena Merriman, of Merriman Events. “We were inspired by Gerda Steiner and Jörg Lenzlinger’s Falling Garden exhibit from the 2003 Venice Biennale, which informed both the floral arrangements and the color palette,” Caroline explains. Given the serious, stately nature of Rosecliff, they also incorporated some whimsy with multicolored Japanese paper umbrellas at the ceremony, gold animal escort card holders, and Happy Menocal’s hand-painted dinner menus.
Early on in the planning process, Caroline knew she wanted to wear all vintage on her wedding day for the sake of sustainability. “When I saw my dress, I knew it was perfect—it was the only thing I found that made sense in such a grand space,” she says. “My mother-in-law gave me the most beautiful sapphire earring-and-necklace set to wear with my dress.” These ended up being her something blue.
For the reception, she enlisted the help of Lily Kaizer of Happy Isles in L.A., who found the perfect beaded gown. She paired it with vintage Chanel four-leaf-clover earrings—for good luck. “I of course picked everything I was wearing with such specificity and care and then completely forgot my shoes in L.A.” Caroline admits. “I called my friend Danica, who was a bridesmaid, at midnight the night before the wedding, and she saved the day—lending me the shoes she wore to her own wedding. It was a such a full-circle moment, as I had helped her put them on on her wedding day, less than a year before. As she put it, I needed my ‘something borrowed’ anyway.”
The ceremony started at 6:00 p.m. on the lawn at Rosecliff. The couple was married under a simple chuppah, with a view of Easton Bay in the background. “We could hear the waves crashing as we said our vows,” Caroline says. “We had a ceremony that included elements of both the Jewish and Catholic traditions, and it was officiated by a family friend who is also a wonderful minister. We wrote our own vows and cried our way through them. Of all of the gifts we have received in our lives, the vows we wrote to each other are our most treasured. I really felt like my heart was going to explode.”
“My worst fear is speaking candidly in front of a large group of people,” Samson reveals. “But when we were up there, I couldn’t have cared less. I felt like it was exactly where I was meant to be.”
Afterward, guests moved inside to the ballroom for the reception. Existing gold tones in the space were complemented with gold stemware and place card holders. Flowers were used to evoke an overgrown garden with fuchsia, coral, and lavender as the primary color palette. “The menu went through many iterations before I finally decided that I would just serve what I would want to eat myself: pasta,” Caroline says. “Guests had a tomato burrata salad to start. For the main course, we had cacio e pepe—my favorite—and short ribs, my husband’s favorite, by Blackstone Caterers.” Aperol spritzes and negronis were served up at the bar. In lieu of a traditional wedding cake, they found a baker in Rhode Island to make a zuppa inglese, which they topped with orange kumquats to complement the color scheme of coral, orange, and purple sorbet colors.
The Sultans of Swing had guests dancing all night. “My dad has MS, and despite being one of the most active people I know, he has to use a wheelchair to get around,” Caroline says. “For our father-daughter dance, he surprised everyone by standing up to dance with me. I am always, but was more than ever in that moment, so blown away by his strength, bravery, and spirit. There wasn’t a dry eye in the room.” Later in the evening, Samson’s childhood friend Rumer Willis gave an impromptu performance. “She surprised us and sang ‘At Last’ with the band,” Caroline says. “It meant so much to us for her to sing for us.” When it was all said and done, the newlyweds couldn’t wait to get back to their hotel room. “Neither of us have ever been so exhausted in our lives, but we were too excited to sleep,” Caroline says. “We stayed up all night ordering deviled eggs and club sandwiches from room service, rehashing every perfect, wonderful moment.”