Before Caitlyn Warakomski and Brendan Slawson built fashion brand HOW DO YOU WEAR THAT, they spent summers working side by side on a golf course. “I was a beverage cart girl, and he was a golf professional at the course,” Caitlyn remembers. “We were co-workers every summer for years before we started dating.”

After 11 years together, Brendan proposed at their beach house on the morning of Caitlyn's birthday in September 2024. Once engaged, the couple began planning a destination wedding in Aruba, where both sets of their parents had honeymooned. “We really wanted to embrace Aruba’s natural beauty rather than compete with it,” Caitlyn says. “I’d describe the overall vibe as intimate, tropical, and, most importantly, fun.”

Planner Annemarie Staluppi of Alongside Annie brought their vision to life, while photographer Sophie Lin Berard and videographer Amanda Films documented every meaningful moment of the spring celebration.

For Caitlyn, the wedding was also an opportunity to design her own bridal wardrobe through HOW DO YOU WEAR THAT, all produced by her team in Manhattan’s Garment District. For the welcome party, she wore Marina Bitu’s Scale Dress—handcrafted from responsibly sourced camurupim fish scales assembled in Brazil—styled with Simkhai heels and Anita Berisha earrings. The following day’s boat excursion called for a custom HOW DO YOU WEAR THAT set paired with a VIX Swimwear suit and a Juju Vera necklace. For the rehearsal dinner, she chose a custom Savannah Miller dress with Sézane earrings, Simkhai heels, and a coordinating bag. Throughout the weekend, the bride and groom approached every look with the same thoughtful eye they bring to their brand.

On April 18, 2026, the Caitlyn wore a custom look by her own brand to get ready in, while makeup artist Marta Collell handled her wedding day beauty. She then changed into a custom strapless two-piece by Alon Livné, paired with a bespoke cape that she designed with Alexis Levan. Anita Berisha earrings, Loeffler Randall shoes, and a Magnetic Midnight pearl fan completed the look.

Brendan put on an Alan Flusser suit, paired with Crockett & Jones shoes. After the ceremony, Caitlyn changed into a pearl-strap top before ending the night in a bespoke dress by Alexis Levan, styled with Brinker + Eliza earrings and Dolce Vita shoes. "When I first started thinking about my outfits, all I could envision was dancing barefoot in the sand in a sparkly kaftan," the bride shares. "This was the perfect combination of glamour and comfort."

At the Hyatt Regency Aruba Resort, Caitlyn walked down the aisle to "Canon in D." "One of the most meaningful parts of the ceremony was having Brendan's best friend, John, officiate our wedding," she says. "There was something so special about being married by someone who knows us both so well."

The newlyweds celebrated with a beachside reception where lanterns were suspended overhead and cane furniture, tropical florals from Naunet Studio, layered natural materials, and string lights all helped define the space, while still letting the beach and ocean remain the focal points.

Chris Kross kept guests on the dance floor throughout the weekend, and the couple shared their first dance to "The Face" by Kings of Leon. "It's definitely not your typical first dance song, but it's always been our song," Caitlyn says. "Looking back, it was probably my favorite moment of the entire reception." As the night went on, a DJ from SwingMasterz kept everyone out on the dance floor.

The after-party continued at the venue's restaurant, Ruinas Del Mar. "It felt like discovering a hidden speakeasy after an evening on the beach," Caitlyn says.

The celebrations didn't stop there. "We actually stayed in Aruba the following week," the bride adds. "Lots of people made it a week-long vacation, so we kept the party going. Come fall, we plan to go to Italy."