Tracy Dubb had no idea that she was setting up future spouses when she suggested that her best friend Selby Drummond, the head of fashion and beauty at Snapchat, meet her brother Steven Dubb, a principal at his family’s real-estate development company. “After about six months of being friends with Tracy, I broke up with my boyfriend and Steven had just broken up with his girlfriend,” Selby remembers. “Tracy said, ‘You know what, you should meet my brother. I feel like you would have fun together. You’re not going to like each other that much—you have nothing in common. You’re not going to want to date. He’s not going to be the person you end up marrying, but you might be able to just have fun and keep it casual.”
Famous last words! A little more than four years later, Selby married Steven in a ceremony overlooking the water at the Cap Juluca Hotel in Anguilla, wearing a frothy custom-made gown by Giambattista Valli. But before the couture dress fittings and the epic late-night dance-off, there was a proposal for the books.
“We dated for a while before we became engaged,” Selby says. “We broke up a bunch of times in the beginning, which was actually the best thing for us.” Steven ultimately proposed in Amagansett, New York, last August. “We were in Long Island, just hanging out at our house, and it was the most normal, calm day. We took a nap; we went for a swim in the ocean. It was the perfect summer Saturday, and it seemed really quiet,” Selby says. At one point, Steven went upstairs and Selby went to the pantry to get some chips. “We were in the middle of watching something bad on TV, and he came downstairs, and he had this red little note in his hand. He shoved the note at me, and he said, ‘I’m leaving now, I’m sending you on a scavenger hunt. Don’t ask questions, don’t call me unless you really need something, and take the truck.’”
Then he disappeared, and Selby stood there holding the chips with no idea what awaited her. She opened the first note, which read: “In Amagansett town, in the square, there’s a shop where we buy coconut oil. Go there and the girl behind the counter might have something else for you.”
She took the truck, drove to the store, and retrieved another note with some Scrabble letters in it and instructions telling her to drive to her favorite restaurant in Montauk. “Initially I thought my birthday’s coming up and we’re playful people, so I thought maybe there was some birthday surprise, but then I realized this was more elaborate than anything he’d done before. I had a feeling, so as I drove myself to Montauk, I started crying and shaking. Apparently he had gone out in the other car and passed me on the road, and I was going, like, 85 miles per hour. I had the windshield wipers on, and it wasn’t raining, the side-view mirrors tucked in, and the back flap of the pickup was just flapping in the wind. He later told me: ‘You looked like a crazy woman rocketing down the road.’ I’m not a great driver; I don’t know why he put me behind the wheel during a proposal, but anyway…”
She arrived at the restaurant where her friend, the manager, told her to keep it together as she handed her the next note, instructing her to “grab the takeout and head to Ditch Plains, where we surf, for another clue.” A surfer had the third note, enclosing even more Scrabble letters, and telling Selby to “come home, I’m in the backyard.” At this point, the letters together spelled out Marry Me. “There were waterworks, obviously!” Selby says. “I probably drove 160 miles per hour back to our house. Honestly, it was the best proposal I could have ever imagined. It was so smart. I’ve always wondered, when men propose, why women are just supposed to all of a sudden say, ‘Yes, I’ve been waiting, no questions asked, I don’t even have to think about it.’ I loved that I had basically an hour and a half to myself to think about how this is what I really want; I’ve been here for four years.”
She got back to the house to find Steven in the backyard with flowers, Champagne, and three balloons tied to the fence. The ring was tied to the string of the last one in the row. “He said: ‘Welcome home! You now have to shoot those balloons down with my BB gun.’”
“Thank God I’m a good shot, is all I have to say!” Selby laughs. “It took me four tries to get three balloons. Steven likes to joke that I shot the last ballon down execution style. Luckily, the ring didn’t fly away or fall in the grass. As he took it, he got down on one knee, and I can’t remember what he said, and he can’t remember what I said, but I know he asked me to marry him, and I said yes! He stood up, we both hugged, and then he said we have some phone calls to make.”
Selby reveled in this moment alone, but Steven kept insisting that they needed to call their friends and family. Finally, he revealed that everyone had been watching her wild goose chase via the iPhone app Find My Friends. They’d seen her driving around and knew she’d been at the house for a while now—but had no idea what the outcome was. “If you don’t call and tell them you’re engaged, they’re going to think you said no,’” he said. “So we’ve got to call these people and put them out of their misery!”
After the calls had been made and the exciting news had sunk in a bit, Selby and Steven set out to plan a relaxed, fun wedding weekend. “We love to surf, we love to be in the water, and we loved the idea of having everyone together—we just wanted one hotel where everyone could be. We’d been to Anguilla a bunch of times, and it’s a really welcoming place. There’s not very much going on other than the water, the sand, the good food, and happy people—and that’s what we cared about. The Belmond Cap Juluca is amazing. They just finished rebuilding and renovating it since [Hurricane Irma in 2017].”
The bride worked with event planners Billy Evers and Julie Freed to create the laid-back atmosphere she’d envisioned. “I certainly would not have gotten through the last eight months without them,” she says. “I had gone to a wedding a few months before I got engaged that Bill had done, so I met them there, and I remember thinking there were the most beautiful flowers and the best invitations I’d ever seen. I thought, That’s probably what I care about. I didn’t know what needed to happen, but I knew I probably cared about good flowers.”
Having spent years working in the fashion department at Vogue, Selby also cared about her dress. “I loved the idea of working with someone who just makes beautiful gowns and beautiful dresses, not typical wedding dresses,” she explains. As luck would have it, she and Giambattista Valli met in Italy at a party a couple of years before she became engaged, and they hit it off. “He loves life, he loves to be out and party, he loves beauty,” Selby says. She had worn one of his dresses to the Met Gala before. “People told me I’d never looked so good, so I actually just messaged him and said, ‘Do you think I could try some things on? I don’t know what I’m thinking yet, but I need to get more information.’” Valli responded saying: “‘Just come to me—and we’re going to do something amazing.’”
Selby supplied inspiration imagery from his most-recent couture show. “If I wasn’t getting married on the beach, if I was having a real, over-the-top wedding, this was the dress I wanted to wear. He had this incredible vision. He drew me a beautiful sketch, and I could see immediately that it was going to be perfect for the location and the setting. He surprised me with something that was exactly what I wanted and exactly right for the moment.”
The celebration started with welcome drinks at Bankie Banx’s Dune Preserve, a bar on the beach situated in a meandering, collaged wooden structure of small wrecked boats and works of art. For this kickoff occasion, the bride wore a Valentino dress she’d loved from the moment she saw it on the runway. Guests spent the evening listening to Bankie Banx, the local legend who played with Bob Marley, setting the mood for the weekend.
On Friday, the day of the wedding, the bride and groom took a dip in the ocean, and then everyone hung around the beach and pool for swimming, volleyball, and inner-tube racing.
At sunset, Selby walked down the aisle, and she and Steven said their vows in a beautiful open-air space, under arches overlooking the ocean. “We had our amazing reform reconstructionist rabbi and our unitarian minister perform our very interesting, modern, interfaith wedding,” she says. After family photos on the steps of the hotel, Selby changed into a dress designed by legendary tailor Bill Bull, and everyone gathered inside the Cap Juluca’s Cipriani restaurant for dinner. “It’s amazing Italian food, which felt right. We eat a lot of pasta and steak, so that’s what we wanted to eat at our wedding,” Selby says. “I didn’t want it to feel too formal or too traditional.” The newlyweds danced to “The Promise” by Sturgill Simpson, as performed by their good friends Dianna Agron and Gill Landry. After the meal, Selby changed into her third look of the evening: a Paco Rabanne minidress paired with Aquazzura heels—and the party really got started with DJ Devin Lucien at the helm. An epic dance-off between Selby’s sister Lucy and the entertainer Beau Jangles ensued. “He should be considered a must-have at any dance party,” Selby says. “He came with our friend and DJ Matthew Mazur and was pretty much the only person who could rival my sister. Although, Steven tried.”
Watch How Giambattista Valli Created Selby Drummond’s Fantasy Dress for Her Wedding in Anguilla:
