Christopher Ivey, co-founder of Jump 450 Media, had just finished his time in the Navy when he first spotted Skylar Shapiro, owner of real estate investment company One Charles, at a party in their hometown in Connecticut. “He followed me around the party like a lost puppy,” she laughs. “And by the end of the night, we were inseparable.” Skylar was only graduating high school at the time, which meant theirs was a long courtship. “We dated for ten years before marrying!” she says.
Their engagement happened during a ski trip in the spring when Chris, an avid snowboarder, asked Skylar to watch him do a trick in the snow. “He went ahead, spun around, and had an extremely pathetic and dramatic fall,” she says. “I made my way over to him and he was laying on the ground moaning about his knee. I asked if I needed to call Ski Patrol when suddenly he had the ring out on the trail and was in full proposal mode. I started kissing and hugging him, which is actually very hard to do when you are strapped into a snowboard!”
Skylar and Chris had spent a lot of their time together visiting her parents’s home in Connecticut, where her mother has a beautiful peony garden. “Peonies have always been my favorite flower so we thought it made perfect sense to get married in her garden,” she says. “We both always wanted to get married outside and the garden aesthetic set the perfect tone for the entire wedding.” They picked June 9th for their wedding day—“full blown peony season!”—and Skylar and her mother got to work on planning all the details. “Having a tent wedding at a private property was way more work than I expected,” Skylar adds. “I began to get really overwhelmed about five months before the wedding so we decided to hire a month-prior and day-of coordinator. I was referred to a company called Just About Married, and we worked with Kait Rovnyak and she was amazing.”
Since she had her hands full with the bulk of the planning, Skylar hired wedding stylist and Vogue alum Cynthia Smith of Cynthia Cook Brides to help with the overall aesthetic. “She was my lifesaver,” the bride says. “She helped me pick out everything from the linens and flowers to what my 7-year-old nephew wore as the ring bearer.” After trying on at least 50 gowns, Skylar eventually found her dress at Carolina Herrera. “It had the most elegant floral appliqué detailing that completely emulated the peonies in my mom’s garden, so I knew it was perfect.”
For jewelry, Skylar wore Jacob & Co diamond studs, and the jeweler also polished her engagement ring days before the wedding so it looked entirely new. She hired Tobi Henney to do her makeup and her longtime stylist at Bumble and Bumble, Chara DeSimone, to do her hair.
Meanwhile, Chris had a midnight blue tuxedo custom made and paired it with a silk black bow tie and blue velvet Del Toro smoking slippers. “He wore gold Burberry cufflinks that I’d bought for him when I worked there,” the bride adds.
For her bridesmaids, Skylar was adamant that they all not wear the same dress. “No one ever wants to show up wearing the same thing to a party, so why would you make your best friends do it?” she explains. Instead, she and Cynthia handpicked a dress for each bridesmaid in a pastel and floral color palette that reflected her individual style.
The day of the wedding, a close family friend officiated the ceremony in the Shapiro’s flower garden. Since there wasn’t any religious element to it, Skylar and Chris organized the entire wedding ceremony themselves, choosing to have their fathers and a few friends perform readings from Winnie the Pooh, a poem by E.E. Cummings, and a passage from Paulo Coelho’s The Alchemist. “For our wedding vows, we actually ended up using a passage from Jane Eyre,” Skylar explains. “A few people asked us if we wrote our vows ourselves because they noticed they were not traditional, but of course we gave Charlotte Bronte the credit!”
After they were married, the couple and their guests headed towards the tented reception. “We wanted the dinner to feel like an intimate backyard party, so we kept the dinner area separate from the dance floor,” the bride says. They served a buffet style dinner of light, fresh, and seasonal summer foods and later treated their guests to music by Eturnity. “I’d heard them play previously at one of my bridesmaids’s wedding back in 2015, and I immediately fell in love with them,” Skylar adds. “I think they were the first vendor I booked right after we got engaged!” As for their first song? “Girl I Wanna Lay You Down,” by ALO, which was one of their favorite songs when the couple first started dating in 2008.
For the after-party, which Chris was adamant about dubbing a “Black Tie to Burning Man” bash, the groom brought glow sticks, neon glow-in-the-dark paint, and feathers, and a DJ provided the entertainment, while Skylar changed into a comfortable two-piece Monique Lhuillier dress. “Our band was absolutely incredible so I don’t think many people were expecting such a fun after-party!” Skylar adds. “Everyone came to brunch the next day still covered in neon paint!”