Gabrielle Truncale of Gabrielle Fine Jewelry and Ryan Sessler first met on a double date—but not with each other. Sparks did not immediately fly, though; instead, they were just friends for several years. Their relationship was a slow burn as they visited each other between Los Angeles and New York. They began dating once Gabby moved to New York permanently in 2023. But by July 24, 2024, they were engaged after a beautifully executed proposal in Greece at the Amanzoe Hotel.
Their planners, Elisa and Elena from K Luxury, took the couple on a four day-long tour around wedding venues in Sicily and Tuscany. “It was one of the most fun and memorable trips of our lives,” Gabby says. “Elisa and the hotel manager at Castelfalfi, Carlotta, were close friends from previously working together and were so excited to show us the property. They saved the best site visit for last.”
It was love at first sight. For the aesthetic, they leaned on their design team at Vincenzo Dascanio Studio to capture the essence of Tuscany and add on to the already magnificent setting. They sent out their spectacular stationery suite by Letterink. The wedding took place all weekend long from September 4 through September 6, 2025 and culminated with the reception on that Saturday. Over The Moon Top Photographer David Bastianoni masterfully photographed the events and Luigi de Gregorio captured everything on film.
For the Thursday night rehearsal dinner, Gabby wore a two-piece outfit from Danielle Frankel featuring the Willow Lace Skirt, the Demi Corset, and the tulle neck scarf paired with an Hermès Mini Kelly in Craie, Jimmy Choo Saeda pumps, and a gorgeous yellow gold bezel set diamond tennis necklace with five-carat pear pendant and diamond studs from London Jewelers. The groom-to-be wore a custom Brunello Cucinelli suit with white pinstripes and suede shoes from Larusmiani.
For Friday night, the bride sourced a vintage 2013 Roberto Cavalli beaded and embroidered dress from Circa Vintage in London and later changed into a mini dress from Sabina Bilenko with Saint Laurent platform heels. She was adorned in a diamond lariat necklace from Noy Tawil Jewelry and earrings from London Jewelers. Ryan wore a custom Brunello Cucinelli sage green double-breasted suit with ivory buttons and ivory shoes from Brunello Cucinelli.
And on the wedding day, the bride wore Danielle Frankel again. She accessorized with a Mantilla veil, Jimmy Choo Sacaria heels, Noy Tawil custom diamond pear-shaped stones choker necklace and pear-shaped drop earrings, and her very own hand chain with their wedding date from her brand. Daniela Delia applied her elegant makeup.
The groom wore a custom chocolate brown tuxedo with black lapels from L&S Tailors in New York City and a flower brooch the bride gifted him from Gabrielle’s brand. Later in the reception, Gabby changed into the Frances dress by Kim Kassas. The custom design featured a removable long lace skirt that could be detached, transforming the look into a lace mini dress perfect for the after-party. Ryan changed into a Brunello Cucinelli white tuxedo jacket and navy satin tuxedo pants for the reception.
In the garden set among the rolling Tuscan hills of the property, the couple wedded underneath a beautiful chuppah. The color palette drew from the earth itself—soft sage greens, warm beige tones, creamy whites, and subtle floral hues with purple allium lining the aisle. Ryan’s five-year-old daughter, Sloane, wore a custom made version of Gabby’s wedding dress from Kashi Couture and was dubbed “The Mini Bride.” She walked down the aisle to a song from her favorite movie, Moana, and ran into Ryan’s arms when she saw him standing at the end of the aisle.
Taking advantage of the brand new ballroom at Castelfalfi—which is not something typically found in most Tuscan hotels—the wedding featured dark red hues roses hanging from the ceiling and chandeliers, red and white checkered dance floor, and the most incredible band, Alessandro De Angelis. Then, the newlyweds sliced into a millefoglie cake they made themselves.
A favorite from the evening was their first dance to the tune of Adele’s “One and Only.” They had worked on the choreography for weeks with Arthur Murray and turned the routine into a full-on show. Sloane even got on the floor with them right after the song ended, grabbed the mic from the band, and directed everyone to join them and “shake their booties.”
The night continued with an after-party at SIZZ, designed to look and feel like a New York nightclub. Outside, there was a red carpet blocked off with velvet ropes and doormen who checked the guest list to let the wedding party in as VIPs. The couple purposefully designed the room to resemble Raspoutine in Paris with velvet couches and a crazy light and sound setup. No detail was overlooked, and espresso martinis and late-night bites fueled dancing well into the early morning hours. One of the guests and couple’s dear friends, Joe Maglia who owns and DJs at MONI in Mykonos, kept the party going with his musical selections.
