Nike Global Senior Brand Director Trelawny Davis first met Amazon Strategy Director Tim Jackowski, when he was invited through mutual friends to her rooftop party in Portland. “We hit it off immediately,” Tim recalls. Just one week later, they went on their first date, setting the foundation for a relationship that would unfold with intention at every turn.
Three years later, that same sense of intention shaped Tim’s proposal. At the end of a trip to Italy for a family wedding, Trelawny believed the evening would end with drinks at a rooftop bar in Florence. Instead, overlooking the Duomo, Tim got down on one knee with the help of his cousins, who were quietly in on the surprise. “I was completely in shock,” Trelawny shares. Italy had always felt special to her, and she never imagined her first trip would coincide with saying yes to forever.
Once engaged, choosing Italy as their wedding destination felt inevitable. “I made a promise to myself when I was really young that I wouldn’t go to Italy until I was in love,” Trelawny says. “I’m pretty sure that promise came from watching The Lizzie McGuire Movie, which is embarrassing—but I somehow remembered it into adulthood.”
With the destination set, Trelawny and Tim focused on finding a venue that would allow their friends and family to stay together while showcasing Tuscany’s natural beauty. With the guidance of Distinctive Italy Weddings, they landed on Villa la Palagina, a countryside estate surrounded by olive trees and rolling Chianti hills. “Once we found it, everything clicked,” the bride recalls.
Guided by her personal style—“classic, chill, and modern,” as she puts it—Trelawny let those three words define the wedding aesthetic. Natural textures, soft hues, and the faded yellow of the villa created an effortlessly elegant setting, brought to life by Fiore all’Occhiello’s floral designs that blended seamlessly with the Tuscan landscape.
Fashion played a thoughtful role throughout the spring weekend. For the vineyard welcome dinner, Trelawny wore a silk Kamperett dress paired with gold kitten heels from The Row and delicate jewelry she had purchased in Rome days earlier. “I wanted something that draped beautifully but felt easy,” she says.
For the ceremony, Trelawny chose a timeless Verdin Bridal drop-waist dress from Bergdorf Goodman. “It was actually the very first dress I tried on,” she shares. The look was elevated with a custom cathedral-length veil featuring French embroidered Alençon lace, handmade by her mother-in-law and aunts of Clarissa’s Boutique in Pittsburgh. A sentimental surprise awaited her that morning as well—a fabric patch sewn into the inside of her gown using material from her great aunt’s 1960s wedding dress, embroidered with family initials and wedding dates. “I will cherish that forever,” Trelawny says.
Beauty was kept natural and minimal with BLBS leading hair and makeup, while Tim wore a custom black tuxedo for the ceremony and a dark olive suit with Gucci horsebit loafers for the welcome dinner.
On June 8, 2025, guests gathered at the villa as the ceremony unfolded overlooking olive groves. A string quartet played “At Last” by Etta James as the bride walked down the aisle with both of her parents. A close friend officiated, making the ceremony personal. “The whole thing felt surreal,” Trelawny recalls. “But I was incredibly present—I wanted to soak up every second.”
Dinner followed poolside, with a menu curated alongside Villa la Palagina’s culinary team. Guests enjoyed Tuscan cheeses during aperitivo, followed by eggplant gratin, cacio e pepe tortellini, and mains including braised short rib, seabass, and cauliflower steak. Dessert featured a classic millefoglie and a layered vanilla raspberry cake by Matimisù di Matilde Sacconi, capped off with fireworks and Champagne.
Music by Kaleydo Entertainment kept the energy high, beginning with the couple’s first dance to “L-O-V-E” by Nat King Cole. One of the evening’s most memorable moments came when a glowing, man-made moon was launched into the sky. “It turned everything into a dream,” Trelawny says. “It felt like a scene from a Wes Anderson film.”
The night continued in a tented indoor-outdoor space filled with disco balls, chandeliers, and draped linens. At midnight, guests were surprised with pizzas, and the dance floor stayed full well past 2 a.m.—all captured by photographer Matteo Coltro and videographer Matteo Di Maria.
Following the celebration, Trelawny and Tim headed to Puglia for a friendmoon with twelve friends before enjoying a short minimoon in Rome. A longer honeymoon is planned for next year—proof that, for this couple, the magic doesn’t have to end all at once.
