College sweethearts Jessica Habich and Matthew Thomas met through the clever matchmaking of mutual friends. “My best friend was dating his best friend at the time, and they insisted we meet,” Jess recalls. “All the girls knew Matt—he was the cute boy on campus—but I didn’t have any expectations.” Though both were young and happily single, they quickly developed a connection that blossomed into something more.
After graduating from Virginia Tech, Jess and Matt were intentional about pursuing their own paths. “We both lived in the city separately with friends and focused on building our careers,” she explains. “It was great for our relationship, but in May 2023, we moved in together.”
Nine years later, Matt got down on one knee on the rooftop of their apartment—a secluded, meaningful space they could access through their kitchen window. The pair had just enjoyed a date at One White Street and returned home to watch the sun set over the SoHo skyline. “It was private and romantic and will always be connected to our very first home together,” Jess reminisces. After the proposal, they headed to one of their favorite bars across the street, where their closest family and friends gathered to celebrate the news.
When choosing a wedding destination, Jess and Matt knew there was only one locale in the running. “Matt and his family grew up going to Montauk to surf all summer, every summer,” Jess shares. “It felt like home when I was missing the city. I think from all of those moments we shared, I knew the town had this really special energy–the kind you want to have at your wedding.”
They invited their 150 guests to Hero Beach Club for the weekend. “We wanted it to feel like Wedding Crashers meets The White Lotus,” Jess jokes. “Just the vibes, not the storyline.” They brought on Over The Moon Editor’s Pick Photographer Lexie Hand to capture every moment.
As a personal stylist, the bride insists that curating her wedding weekend wardrobe was the most fun part of planning. Jess put together seven distinct looks that felt like her very own bridal collection.
To kick off the weekend, the bride made a splash in a vintage ’90s Ferré number from Happy Isles, which was transformed into a chic mini dress for the welcome party. To elevate the look, she repurposed the remaining fabric to create a matching headscarf. The following evening, Jess slipped into a two-piece by Kettel Atelier, hand-sewn entirely from deadstock lace. A pearl-adorned éliou choker and a CHANEL bag from her mother-in-law completed her rehearsal dinner look (and checked the box for her “something borrowed.”)
On the morning of the wedding, the bride wore a Fait Par Foutch skirt set alongside her bridesmaids, who were styled in vintage white slips and feather boas Jess had collected from secondhand stores over the years. For the ceremony, she wore a Leah Da Gloria drop-waist dress paired with a lace, three-tiered veil by Rime Arodaky. After her fitting, she removed the train—but rather than discarding the excess material, she collaborated with Samraye Studio to transform the silk taffeta into a bouquet she could cherish forever.
Despite a background in fashion, Jess never expected to design her own reception look. She started in a custom creation for the reception and then changed into an after-party dress from the Valentino Spring/Summer 2024 Collection, which she accessorized with a headscarf that featured matching floral appliqués. For the wedding day, Matt looked handsome in a Calvin Klein tux paired with Fendi loafers, two vintage brooches layered on his lapel, and his grandfather’s cufflinks.
To ease any pre-wedding jitters, Jess and Matt kicked off the weekend with an all-day surf session and the famed Goldberg's Bagels. “Watching Matt in the water has truly become the most joyous and therapeutic pastime of mine, so much so that I’ve learned to love to get out on a board myself,” Jess says. “We called the theme of our wedding ‘Apres Surf’ because after a day on the water, we hosted a black-tie wedding at a motel on the beach of *insert our opinion* the best surf town in the U.S.”
On the 21st night of September, the couple’s priest performed the wedding in Montauk just a short walk away from the reception venue. “Matt and I were both raised Catholic, so it was important to us and our families to recognize our marriage in the church,” Jess shares. “There aren't really words to describe how holy and connected I felt to both Matt and God in that moment.”
After cocktails, the newlyweds shared their first dance to a rendition of “Yellow” by Coldplay, performed by the 10-piece band, Rhapsody. After a delicious dinner by Montauk Catering and heartfelt speeches from the maids of honor, Matt’s best man, and both fathers, guests enjoyed espresso martinis, Bon Bon candy, and french fries on the dance floor. "My dad is an incredible singer and guitarist, so he hopped on with the band and played “Running Down a Dream” by Tom Petty and “I Melt with you” by Modern English," Jess gleams. "The crowd went wild–it was absolutely epic.”
Just as they thought the energy was at its peak, “September” by Earth, Wind, & Fire sent the crowd wild. “I started thinking about how crazy it was that we were actually getting married on this night, the eve of my grandparents' anniversary,” the bride reminisces. “My parents got married on September 23rd, so it was as close to a tradition as it could be.”
To keep the party going, the couple and their guests headed to their favorite dive bar, Memory Motel, where they partied into the wee hours of the night. “The next morning, people were running to the ocean, giggling over coffee in the lounge, and looking for their shoes and phones in other guests' rooms,” she says. “It was exactly what we wanted. . . one massive sleepover.”
