Stunning City Views and Eccentric Decor Brought This New York Wedding to Life

Kristin Simmons and Matthew Cimaglia’s slow-burning romance started while they were volunteering on a video project for a nonprofit—Matthew helped with production, while Kristin assisted with the creative direction. They met for coffee and dinners, sent each other witty texts and talked endlessly about their shared love of aesthetics. But their connection didn’t immediately blossom from there.

It wasn’t until two years later that the duo decided to have a romantic dinner date. Skip to five years later, and during a walking tour as church bells rang, Matthew proposed to Kristin in Korčula, a stunning Croatian island in the Adriatic Sea. There was even an engagement photographer there to capture the moment, whom Kristin initially thought was a random tourist. “There were cheers, tears and Aperol spritzes,” the bride recalls.

The couple wanted their June wedding to feel like “stepping into someone’s weird, joyful, overly sentimental dream” and to “inject a sense of humor and personality into every detail.” To achieve this, they turned their celebration into a surreal, modern-art experience. On the rooftop of the 620 Loft & Garden, Kristin and Matthew exchanged vows with the St. Patrick’s Cathedral in the background and a vibrant rainbow of peonies, roses, alliums surrounding them. The cocktail hour followed at the 610 Loft & Garden, where a huge art palette adorned with blooms was the focal point and tasty espresso martinis and light bites were served.

As guests entered the inside of the venue, they were greeted with a full display of Kristin’s creative side and dedication to personalization. Every wall was decorated with the bride’s playful doodles of lobsters, wedding cakes, cherubs and chandeliers. She also made hand-drawn escort cards that depicted each loved one and custom place cards that were decorated with adorable illustrations, which complemented the pastel-colored napkins, taper candles and flower arrangements on each table.

And the night didn’t stop after the whimsical dinner. There was a fake cake display with numerous lambeth-style confections that had quirky messages on them. And when it was time for dessert and dancing, the party was transformed to a “celestial chic” theme with hues of navy blue, gold and silver throughout, star-shaped lanterns and a hanging installation of white hydrangeas that resembled a fluffy cloud. “Every inch of it felt like an art installation disguised as a wedding. It was deeply unserious, meticulously thought out and unapologetically ours,” the couple says.