Olivia Dilorati and Jay Matthews’s wedding unfolded as a thoughtful extension of the life they’ve built together. Though the couple officially married in an intimate Catholic ceremony on Martha’s Vineyard earlier in the week, it was on October 5, 2024, that they gathered their wider community for a garden celebration at Lambert’s Cove Inn.
The couple’s story began years earlier, when Olivia and Jay attended high school together outside Boston. It wasn't until they reconnected around their five-year reunion that they officially began dating. What followed was a seven-year relationship shaped by long distance, shared history, and a deep sense of ease—one that eventually led them back to the places that mattered most. Jay proposed on Martha’s Vineyard in August 2023, at a beach Olivia had grown up visiting with her family. “It was such a special night on Martha’s Vineyard with our families,” she recalls.
When it came time to choose a wedding setting, the island naturally resurfaced. While the couple briefly considered New York City, they ultimately returned to the Vineyard, where Olivia’s family history and Jay’s Massachusetts roots overlapped. Lambert’s Cove Inn stood out immediately. “The boutique hotel has an English country style feel that is elevated and charming, while also feeling cozy and comfortable,” Olivia explains. “That was the kind of environment and aesthetic we wanted to create for our guests.”
The planning and design, orchestrated by Benor & Beik, leaned into that sensibility, allowing the setting to lead. Garden paths were framed with tapered florals, and outdoor spaces felt layered rather than overly styled, as if they had evolved organically around the celebration itself. Florals by Morrice Florist echoed the season in soft, earthy tones that complemented the inn’s wooded grounds without overpowering them, while Over The Moon The List Photographer Trent Bailey and videographer Johnny Havens captured the weekend with a quiet, observational eye—preserving not just the beauty of the setting, but the relationships at its center.
Olivia’s fashion choices reflected that same sense of balance. She had long envisioned a high-neck lace dress—something classic but not severe. Once the venue was confirmed, the direction was clear. She worked with designer Sam Walls of Samuelle Couture to create a custom look. “It was sophisticated with the high neck, but also sexy with the open back,” she says. Being involved in the process became one of her favorite parts of planning: “The end result was so beautiful—I didn’t even want to take it off at the end of the night.”
Sentiment guided her accessories as well. Olivia wore diamond earrings gifted by her parents and pearl jewelry passed down through her family—pieces that quietly carried memory without calling attention to themselves. The bride's hair and makeup was done by Sea Spa Salon, who kept the look soft and natural, allowing the lace and silhouette to remain the focus.
The ceremony took place in the garden, where guests gathered along a floral-lined aisle. Music by The Dukes set the tone, with acoustic arrangements that felt intimate. A close friend officiated, keeping the atmosphere calm and grounded. “Her presence up at the altar with us kept us calm and relaxed,” Olivia says.
Writing their own vows was a priority. “I thought I would be nervous, but when I got up there, I didn’t think about anyone else except for Jay and me,” she recalls. “We had a handful of people come up to us after saying our vows were super special and meaningful.”
After the ceremony and an alfresco cocktail hour, guests moved into the reception tent. “Walking into the tent for the first time truly was beyond anything we could have imagined,” Olivia says. “Seeing all of our closest family and friends standing up, smiling and laughing as we walked in—we were blown away.”
The evening unfolded with ease. Live music carried the night, dancing spilled between moments, and the energy stayed buoyant well past dinner. “We wanted everyone to feel comfortable, mingle, dance, and just enjoy,” Olivia explains. “Our guests danced all night long, even in between dinner courses, which is what we wanted.” As the night stretched on, the celebration naturally shifted indoors, where late-night dancing and casual bites kept the momentum going.
Looking back, what stands out most is how present the day felt. “We both felt relaxed and just were so excited to be there,” Olivia says. “We both felt very present—which was all we could have asked for.”
