The Bride Wore a Dress Designed by Her Best Friend to Marry at a 200-Year-Old Estate in Portugal

In the lead-up to the wedding, both Madison and Lex threw themselves into the planning process—and kicked off their journey by reading The Art of Gathering by Priya Parker, which served as their guide. “From the start, we set a clear intention,” Madison explains. “Our wedding wasn’t just going to be a party—it was going to be about building our future community. Priya talks about the sweet spot for building a community being around 150 people and encourages avoiding ‘legacy’ invites—those people you feel obligated to invite because of your parents or the past.” As a result, the couple broke with traditional wedding rules and followed the book’s advice. “Every decision we made—who we invited, how we seated guests, the moodboards, even the dress codes—was intentional and centered on the energy and people we want in our lives as we start this next chapter together,” Madison adds.

The couple enlisted Molly O’Rourke and Jeffy Hnilicka to plan their wedding weekend. “They are the best duo on the planet,” the bride says. The wedding weekend started with a vibrant welcome celebration dubbed “A Lively Festival” on Thursday night. The theme? More Is More. “Think bright, warm colors—yellow, orange, red, and pink—mixed with bold, contrasting combinations,” Madison says. Guests embraced colorful patterns, maximalist prints, and accessorized with feathers, fringe, crowns, masks, brass, leather, belts, bells, and all things glitter and gold.

When beginning to plan her wedding weekend looks, Madison made a pact with herself: Every evening outfit had to be as sustainable as possible. This meant custom pieces made from deadstock fabrics in New York or vintage-sourced finds. “It wasn’t always easy, but it was so worth it,” she says. A vintage Alexander McQueen Irene dress from his 2001 Shipwrecked collection served as her first look. “I found it on 1stDibs and later discovered it was sourced through Tab Vintage,” Madison says. “It inspired me to take a trip to L.A. to visit their studio for more looks.” She paired the dress with earrings and a bracelet by Mejuri and Amina Muaddi shoes.

For the rehearsal dinner on Friday, the couple wanted a light, romantic atmosphere to honor the coming together of their family and friends, with a palette of whites and neutral tones and minimalist and uncomplicated decor. To echo the theme, Madison wore a custom One / Of dress made from deadstock lace by designer Patricia Voto. “Patricia and I explored so many sketches before landing on using Zoe Kravitz’s iconic Met Gala look for design inspiration,” Madison remembers. “The one long sleeve shoulder, with the super high leg slit made the dress both appear modest and insanely sexy. I loved the entire process, and Patricia was a dream collaborator. She truly understood my vision and brought it to life with such care and precision.”

The next day, the ceremony took place in what was the farm estate’s family garden for almost 200 years. The space features a long stone walkway, creating a dramatic runway for the groom and his mom and the bride and her father to walk down the aisle. “In the hour leading up to the ceremony, the sky was a heavy gray, which was surprising after such a beautifully clear day,” Madison remembers. “I had completely surrendered to the idea that it might rain—after all, we were outside in the middle of nature, and you can’t control the weather.” Just as the ceremony began, however, the clouds began to part. “By the time I was reading my vows, a beam of sunlight broke through and hit my back. It was a surreal, almost magical moment that felt bigger than us. As my friend RJ King so beautifully put it: ‘It was as if the people watching over Lex and me—whether the universe, fate, or loved ones we’ve lost—were holding back the rain just long enough for us to say our vows and seal our union.’ By the time the ceremony ended, I felt such an overwhelming sense of gratitude, not just for the weather but for everything the moment represented. It truly felt like a blessing.”

For her walk down the aisle, Madison wore a one-of-a-kind wedding dress designed by her best friend Elsa Hosk for her brand Helsa. “This was Elsa’s first and only wedding dress, which made the whole experience even more special,” Madison says. “It was such an emotional and personal process—going through the highs and challenges of creating a gown with someone who knows me better than almost anyone.” The dress itself featured pleating, drapery, and a back bow—and “fit perfectly,” according to Madison. “It was timeless and classic but still felt so me. Wearing something made by Elsa wasn’t just about the dress—it was about the friendship and love behind it.”

As an additional focal point during the ceremony, the couple had Bosque Concepts, a Lisbon-based design studio, create an avant-garde mirrored beam sculpture. “The sculpture was designed to reflect back to us—and to our community—the idea of our future together,” Madison explains. “It added such a powerful, symbolic layer to the ceremony. The entire experience was deeply romantic, surreal, and breathtakingly beautiful. There wasn’t a dry eye in the crowd—it felt like every single person was fully present, sharing in the love and connection of the moment. I’ve never felt more loved, supported, or held in my life than I did right then.”

After the ceremony, it finally rained. “The weather held out just long enough for the ceremony, but right after, the rain came down,” Madison says. Cocktails were moved into the venue’s former apiary, or beehive yard, which had a rustic feel. This was followed by the reception and dinner, which took place in a futuristic, custom-built chrome tent with a high ceiling—designed to make it feel like everyone was still outside. The bride changed into a vintage 1930s wedding dress sourced from Tab Vintage paired with Agmes earrings. The liquid silk gown featured long sleeves, a train, and hand-beaded shoulders. “It felt like it was made for me,” Madison says. “I’ve been wondering about the original bride ever since. I worked with Tatiana Kova Studio in New York City to raise the neckline for a high-neck, vintage-inspired look. Tatiana is a genius.”

After dinner and dancing, the couple threw an after-party with DJ Zee Muffin and DJ Khalil who came from New York City. “It went very late—in the absolute best way. It was pure magic from start to finish,” the bride says. Towards the end of the evening, Madison changed into her final look of the night—an ecru Dior mini dress with an embellished ruffle from 2008 to dance the night away.

“It really was the best weekend ever. No notes.” Madison says. “Everything turned out exactly as it was meant to and even better than we could have imagined. We broke most of the wedding rules and did everything our way. By designing the weekend around building our future community, we ended up with the most amazing dynamic. Watching people from all parts of our lives come together and forge their own friendships was truly a dream come true.”