Brooke Botsford, President & CEO of InsideHook, a digital lifestyle company for men, met William Sinclair, an executive director at J.P. Morgan, unexpectedly at a restaurant in New York City. “My good friend, Paige Pedersen, and I were catching up over dinner at Le Bilboquet,” explains Brooke. “We were seated next to William, who happened to be a friend from Paige’s hometown of Greenwich, CT. Our tables began chatting, and by the end of the night, William and I had set up a dinner date of our own!”
Fast forward two years, and the couple became engaged on a beach in Massachusetts. “My family has a summer home in Osterville, and William’s parents were joining us for the weekend,” remembers Brooke. “Early on Saturday morning, William and I took off for our favorite bike ride down Sea View Avenue to The Cut. We hopped off of our bikes to look at the ocean, and the next thing I knew, William was down on one knee proposing. It was perfect.” The pair spent the rest of the weekend celebrating with family.
Determining the wedding’s location was an effortless decision for the duo. Since she was a young girl, Brooke had dreamed of a reception at the Yacht Club in Newport, RI, and as a St. George’s School alumnus, the campus chapel was a natural choice for the ceremony. “Plus,” Brooke adds, “many of our guests live in New York, Boston, and Greenwich, so it was an easy weekend destination.”
When it came to the dress, the decision wasn’t as simple. “I must have tried on about 50 different options before I came across a stunning Oscar de la Renta dress online,” says Brooke. “It proved to be quite tricky to track down, but once I did, I knew I’d found ‘the one.’” To complement the dress, Brooke wore light pink Manolo Blahnik shoes, found with the help of her mother, and Mikimoto diamond and pearl drop earrings, a wedding gift from her father.
Shortly after guests arrived on the hilltop and gathered in the English-style gothic chapel, Brooke walked down the aisle to “The Prince of Denmark’s March” by Jeremiah Clarke. “I love the way the chapel pews face each other,” Brooke says. “It was so fun to see all of our loved ones as my dad and I made our way to the altar.”
Father John Rick, who married Brooke’s parents, led the traditional ceremony. The couple wrote their own heartfelt vows, and readings were delivered thoughtfully by close family members and friends.
Following the ceremony, the black tie affair kicked off with cocktails on the harbor, where passed sliders proved to be a big hit. For dinner, guests made their way into an elegant tent to enjoy local tomato and grilled corn salad with shaved manchego, followed by pan roasted filet mignon. White and green flowers decorated each table, and trees glowing with string lights added warmth to the ambiance. The father of the bride, along with the matron of honor, Libby, and best man, James, all gave heartfelt and entertaining toasts.
When it was time to hit the dance floor, Simply Irresistible, a 14-piece band from Atlanta, kept the party on their feet. “DJ Khaled’s ‘All I Do Is Win’ was the song that got all ages out on the dance floor,” laughs Brooke.
The reception concluded with fireworks over the water and a quick wardrobe change in anticipation of the after-party. (Brooke slipped into a more dance-friendly Monique Lhuillier dress.) “Although, the hemline turned completely black by the end of the night,” Brooke admits. For their send-off, the newlyweds departed by boat. After stealing a few moments alone while crossing the harbor, the pair arrived in town to continue the celebration at Sky Bar in the Clarke Cooke House. “I can’t imagine a more magical way to end the best day of our lives,” reflects Brooke.