Jesse and Joe first met aboard a four-day cruise called Jewbilee, where an unexpected dinner conversation and plenty of shared gossip about fellow passengers sparked an instant connection. “My first impression of Joe was that he was a very good-looking nerd,” Jesse recalled. While she wasn’t looking for forever at the time, his kindness, humor, and compassion slowly won her over. One year later, they were living in New York together, and by the following September, Joe proposed in their first home with a cherished family heirloom ring.
As a wedding planner herself, Jesse approached planning with one guiding philosophy: if something feels fun and authentic, it’s worth doing. Rather than following trends, the couple embraced every wonderfully unconventional idea that reflected their personalities, creating a wedding at Saugerties Performing Arts Factory that felt equal parts whimsical, theatrical, and deeply personal.
The wedding vision
From the very beginning, the celebration promised something refreshingly unexpected. Built around a “whimsical disco” concept, the wedding – photographed by William Thomas Photo – blended playful fantasy with elevated design.
Rich shades of coral, peach, pink, and red carried guests through every space, while imaginative details transformed familiar wedding traditions into joyful moments of surprise. Every decision reflected the couple’s willingness to celebrate exactly as themselves.
On trend: Basque waist wedding dress
Jesse found her Julie Vino wedding gown in the very bridal salon where she had once attended a professional event, this time returning as the bride.
After trying on only two dresses at Nicole Bridal, she discovered the one: an allover lace gown featuring a romantic basque waist and the slightly daring silhouette she had envisioned. Delicate lace wristlets completed the look, adding a distinctive editorial finish that felt both timeless and fashion-forward.
Showstopping custom groom’s style
Joe’s attire was every bit as memorable. Designed exclusively by his friend Andre Landeros, his custom silk faille suit in a vibrant coral hue featured the designer’s signature oversized button-up sleeves. The bold look perfectly complemented the wedding’s colorful aesthetic while celebrating Joe’s own sense of style.
A ceremony that blurred reality
The ceremony blurred the line between reality and fantasy.
Guests were seated on striking ombré chairs that introduced the vibrant color palette before their eyes were drawn to a transparent lucite chuppah from Matthew James Design surrounded by oversized paper flowers by Seasons on the Hudson.
The dramatic installation created an almost floating effect, transforming the ceremony into something that felt delightfully theatrical while remaining deeply meaningful.
Jesse’s brother officiated the ceremony alongside a female rabbi, thoughtfully honoring the couple’s Jewish traditions while reflecting the people most important to them.
A paper airplane ceremony exit
After exchanging vows, guests participated in one of the day’s most playful traditions. Rather than tossing petals or confetti, they launched colorful paper airplanes into the air, each coordinated to the wedding’s vibrant palette. The whimsical moment perfectly reflected the couple’s playful spirit and created a joyful conclusion to the ceremony.
A “shady” escort display
One of the most memorable design moments paid tribute to the couple’s own inside joke.
Inspired by their love of “spilling the tea,” the escort display featured colorful sunglasses assigned to each guest alongside the cheeky instruction: “Be seated…and be shady.” Equal parts functional and hilarious, it immediately invited guests into the playful world Jesse and Joe had created.
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Detail we love: fringed ceiling installations
The celebration continued with imaginative details around every corner.
Fringed ceiling installations introduced movement and texture overhead while the warm palette of reds, peaches, and pinks carried seamlessly into the reception design.
Every element embraced maximalist creativity without losing its sense of cohesion, resulting in a celebration that felt artistic, immersive, and unmistakably their own.
The entertainment: a celebrated NYC drag queen
Entertainment became one of the defining highlights of the evening.
Before the wedding, guests were invited to anonymously submit personal confessions, which were transformed into a humorous live performance during dinner by celebrated New York City drag queen Shaquida Hall. For Jesse, a longtime admirer of drag culture, incorporating such an iconic performer into the celebration felt especially meaningful.
The evening unfolded with laughter, surprise, and the kind of joyful energy that only comes from creating a celebration without limits.
A wedding that refused to blend in
Jesse often encourages couples to stop worrying about whether an idea feels “too different.” Her own wedding became the perfect example of that philosophy in action. From custom fashion and fantasy-inspired ceremony design to drag performances, paper airplanes, oversized florals, and tea-themed escort cards, every detail reflected two people who weren’t afraid to embrace what made them unique.
The result wasn’t simply a beautiful wedding—it was a celebration filled with personality, creativity, and the confidence to make every decision entirely their own.
