This Supper Club-Themed Wedding in Virginia Will Make You Wish Tomato Girl Summer Never Had to End

A little more than a year after Cory and Chelsea met on a dating app, he surprised her with a flower- and candle-filled proposal on the rooftop of their New York City apartment after dinner at their favorite sushi spot.  Their August engagement and early summer wedding date—June 29, 2024—inspired a vibrant design based on an unexpected source: juicy red, yellow, green, and orange heirloom tomatoes. Planner Laura Ritchie of Grit & Grace complemented their “tomato girl summer” aesthetic with a chic, urban speakeasy theme, infusing every part of the day with the couple’s bold personality and meaningful details. "We wanted it to feel as ‘us’ as possible,” says Chelsea. “A summer supper club with our nearest and dearest all being in the same place to celebrate over many days!”

The couple hosted 160 guests at Salamander Resort in Middleburg, Virginia, for their wedding on June 29, 2024. “We had the absolute best time planning our wedding, which is all due to having Laura behind the wheel,” says Chelsea. “We leaned into working with women-owned businesses who had familiarity with the venue and connected with the aesthetic. If you ask any of my friends, they would say that I was truly on cloud nine during the whole process.”

Intentional choices were made on the fashion front, too: Chelsea designed the custom wedding dress she’d always envisioned, while Cory finished his look with heirloom accessories from his parents and grandparents. The duo also incorporated their favorite foods—from oysters during the cocktail hour to Chelsea’s favorite pickles on a stick as a late-night snack—and added hand-drawn illustrations, monogrammed details, and bespoke linens throughout their reception. Even the welcome boxes created by the bride’s mother included an extra personal touch: A family friend contributed 75 loaves of fresh-baked banana bread, one for each box. 

The wedding weekend began with a rehearsal dinner for the couple’s immediate family, where Cory and Chelsea’s nieces and nephews played games on the lawn while the adults toasted to the couple’s future together. “Our families have become very close over the last few years,” says Chelsea. “Make sure to remember what it is all about—starting your life with your partner—and treat the whole process like it’s a celebration! The whole engagement period is meant to be fun and exciting, not just a means to a perfect weekend, so slow down, find joy in each moment along the way, and try not to sweat the small stuff.” Ahead, see every joyful, over-the-top theme in these energetic images by Lisa Ziesing with Abby Jiu Photography.

As Maryland natives, Chelsea’s family was familiar with the pastoral landscapes, well-known culture, and small-town charm of Middleburg, Virginia. The spacious Salamander Resort offered exactly what the couple hoped for: “We wanted a place that our guests could come and spend the weekend together with all events on the same property for an upscale, ‘camp’-type feel,” says Chelsea.

Kelsey Maile Design created an invitation suite that brought the couple’s “tomato girl summer” theme into vibrant focus, incorporating the heirloom fruits’ iconic shades of red, yellow, and green. Accents of pale lavender and bold cobalt allowed the suite’s signature scallop shape—a subtle nod to the outline of a sliced tomato—to pop on the envelope liner and welcome party card.

After holding a family-only rehearsal dinner on Thursday, Chelsea and Cory hosted a welcome party for all their guests on the night before the wedding. Cory donned a beige linen suit from Suitsupply, while Chelsea followed the “chic and colorful” dress code in a Khaite silk slip dress printed with rich red puckers. The bride’s Badgley Mischka heart-heeled shoes added to the feeling of love in the air.

Guests celebrated with food and drinks around the resort’s outdoor pool as the couple marked another family milestone: Chelsea’s grandmother Sandi’s 85th birthday. “This was a big consideration when we chose our date, since Nana is a huge part of [our] lives,” says the couple.

Chelsea worked with her hair and makeup artist to create a look that “was centered around looking like me, but elevated and bridal!” she says. After trying multiple hairstyles before the big day, she settled on a low, sleek bun that would keep her hair off her neck in the late-June heat—but on the morning of the wedding, she adjusted the plan. “When I sat in her chair on the wedding day, I changed my mind and told her I wanted to wear my hair down, as that felt more ‘me’ (despite the 90-degree heat),” says Chelsea. “With very little discussion needed, she completely understood what I was going for and ended up with a very bridal, yet very ‘me’ look that I absolutely loved.”

Chelsea—a self-described “huge skincare fan”—diligently followed a pre-wedding regimen that included monthly facials, dermaplaning, and an at-home routine with Dr. Dennis Gross and iS Clinical products. “I am big on my Dr. Dennis Gross LED mask and used it nightly leading up to the wedding,” she says. “My Revision lip replenisher was always with me for lip prep before the big day, too.”

Chelsea teamed up with designer Elizabeth Fillmore to create a custom slip wedding dress with a sleeveless, high-neck beaded overlay. “When we went into her atelier, I talked through with her what I had envisioned, which was similar to a few of her gowns but something she had never done before,” says Chelsea. “Standing in her studio, I had the bottom part of one dress on, with a second dress over top to show the combination of the two. I stood there as she and her husband were holding pieces of fabric around me as we Frankensteined the dress together, and ultimately decided it was a winner before ever truly being able to envision it.” 

At a fitting two weeks before the wedding, Chelsea finally saw all the pieces come together—and then requested a major last-minute change: removing the original long sleeves. “I had always envisioned the overlay to be sleeveless, high neck, and beaded top to bottom,” says Chelsea. “When I tried it on that way for the first time, it was truly like seeing my original vision come to life.”

Chelsea asked her sister to be her maid of honor, while Cory’s two best friends were his best men. “Otherwise, we didn’t have a traditional bridal party and instead had our immediate family very involved in the wedding,” says Chelsea. “Each of our siblings (and siblings in-laws) walked down the aisle with one of our five nieces and nephews; our sisters gave the reception speeches, along with my parents, and my brother and sister-in-law handed us our vow books during the ceremony.”

Cory’s custom Suitsupply tuxedo included a tomato-red lining embroidered with the couple’s shared initials and wedding date. He included accessories with sentimental connections to his family: cufflinks with a B initial from his father; his late grandmother’s handkerchief—a wedding day surprise from his sisters—that he wore as a pocket square; and his grandfather’s gold wedding band.

After having breakfast together on the morning of the wedding, Chelsea and Cory dressed separately and then met for a first look before the ceremony. “We wanted to be able to spend as much of the wedding day together as possible,” says Chelsea. 

They chose the venue’s verdant culinary garden for a backdrop, but tweaked the typical first look format. “Instead of tapping Cory on the shoulder to turn around per a traditional first look, we wanted him to watch me walk up to him from afar so he could see my whole look and then take it in as I got closer,” says Chelsea. “It was really special.”

The venue’s sprawling lawn offered enough space for the couple to create a ceremony-in-the-round setup, with a square structure enclosing the couple as they said their vows and guests sitting on each side. Sweet Root Village created “ground-growing florals with sprawling, wild, and funky sections of color and texture,” incorporating spider gerbera daisies, clematis, yarrow, and tomato vines in the red, peach, orange, and yellow color scheme.

Sage String Quartet performed Frank Sinatra’s “Fly Me to the Moon”—Chelsea’s late grandfather’s favorite song—for the wedding processional before shifting into Billy Joel’s “Vienna” as Chelsea’s parents escorted her to the altar.

After exchanging handwritten notes on the morning of the wedding, Chelsea and Cory also shared their own vows during the wedding ceremony—inspiring ”lots of tears in the crowd,” says the bride. The newlyweds beamed as they walked down the aisle after the ceremony to “Lose Control” by Teddy Swims.

One of the couple’s favorite details was an escort display of juicy summer tomatoes calligraphed with guests’ names. Pink trellises lined the walkway in the culinary garden, highlighting the tomato girl summer-inspired color palette.

Chelsea and Cory lined the walls of the dining room with two-toned pink draping that set the tone for their colorful speakeasy aesthetic. The décor included an unexpected touch from the father of the bride: “[I] had dreams of covering the ballroom carpet to transform the space, and my dad worked with Laura to surprise us,” says Chelsea.

Hand-drawn placemats anchored the design of the couple’s long rectangular tables, where orange table lamps added to the supper club vibe. Blue glassware, knotted pink-striped linens, cobalt-handled flatware, and warm florals finished the vibrant design scheme.

Round tables were covered with custom pink-and-red striped linens and lit by petal-shaped pendants that matched the black-and-cane seating. Circular menu cards in a variety of color palettes were illustrated with high-contrast sketches of red and yellow tomatoes and framed by green-and-pink patterned napkins.

A custom-painted pink bar included decorative panels with hand-drawn illustrations of cocktail glasses, garnishes, tomatoes, and the couple’s monogram; stirrers, napkins, and matchbooks displayed on an acrylic lavender tray were accented with bunches of petite cherry tomatoes.

Chelsea and Cory chose "May I Have This Dance?” by Francis and The Lights, featuring Chance the Rapper, for their first dance. “We did a choreographed dance—somewhat reluctantly, but it ended up being so fun,” they say. 

Sharing their day with only 160 guests posed one of their biggest wedding planning challenges. “Cory and I and our parents love to be surrounded by our people, and we all have a ‘the more the merrier’ attitude, so it was difficult to not extend the invite to everyone in our broader circles,” says Chelsea. After all their efforts to keep their guest list from expanding, they ended up hosting two extra attendees: unexpected wedding crashers who left the couple a card containing $11.54 from “Uncle David and Aunt Nancy” (before they were escorted out).

Chelsea spent months looking for a white, party-ready reception dress that would be easier to dance in than her wedding gown, but then she embraced a new vision. “I had an epiphany that with the whole wedding being a bright and vibrant display of color, with red as a constant in our décor, I should wear red!” she says. She found a tomato-red mini dress with sequined heart embellishments from Area NYC. “It felt like a perfect fit for the occasion: red for the theme, hearts for love, and just very me,” she says.

Late-night snacks included sliders, truffle fries, and the couple’s favorite New York City snack: pickles brought directly from their favorite Bryant Park vendor, Pickle Me Pete. The evening ended later than expected thanks to another sentimental family tradition continued by Chelsea’s father, who capped off the personalized affair by asking the band to continue for an extra hour, into the after-party—”like my grandpa Papa, who passed away November 2023, did for [my dad and] my mom’s wedding,” says Chelsea.