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Inside Olivia Culpo and Christian McCaffrey’s Classic New England Wedding

In 2019, a mutual friend set Olivia Culpo and Christian McCaffrey up on a blind date.

Photo: Jose Villa

When she walked into a San Diego hotel lobby to meet him for the first time, he was holding a bouquet of flowers, and as they talked, Olivia was quickly charmed by Christian’s kindness and humor. She had recently written in her journal a list of the qualities she was looking for in a partner and realized he checked every box. “After that night we were inseparable,” she says.

Four years later, Christian, a San Francisco 49ers running back, and Olivia, a model and former Miss Universe, got engaged during a road trip to Utah. “Christian should get an Oscar for his acting skills because I had absolutely no idea he was proposing,” Olivia says, laughing. “He was so good at convincing me that he wasn’t ready.” Secretly, he’d been planning a proposal for months: After driving an RV through the red-rock desert, the two arrived at the Amangiri hotel. That night, an employee brought Olivia into the middle of the desert for what she thought was a casual sunset cocktail with Christian. “When I walked up, there were the most beautiful flowers surrounding the area and a gorgeous sunset,” she says. “I’ll never forget Christian turning around and saying, ‘This is long overdue.’ He got down on one knee, and I started to cry.”

Olivia always knew she wanted a traditional wedding in her home state of Rhode Island. After deciding to marry on June 29 at Ocean House, a historic resort in Watch Hill, she asked Lisa Vorce to be her wedding planner. Vorce completely understood her vision and allowed her to be present, according to Olivia. “I tried to remind myself that this could very well be one of the last times Christian and I have every single one of our loved ones in one place,” she says of the planning process. “I tried to keep gratitude at the forefront.”

She then asked Dolce & Gabbana to design her wedding dresses. “I had a very clear idea of what I wanted for my ceremony dress,” Olivia explains. “I have worked with Dolce & Gabbana for years, so it was incredibly special to collaborate with Stefano [Gabbana], Domenico [Dolce], and the exceptional design and atelier team.”

Olivia and Christian’s wedding weekend began with an intimate dinner with their two families on Thursday, June 26. The next night, they had a welcome dinner for all guests on the lawn of Ocean House, which they turned into an Amalfi Coast–style garden. “It was the most beautiful blue-and-yellow color story, and the evening combined my New England background with my Italian heritage,” says Olivia. She wore a Dolce & Gabbana chiffon dress with bishop sleeves. As the night progressed, guests headed into the hotel’s Bemelman Gallery, which Olivia and Christian had turned into an espresso-martini lounge. Several of Olivia’s former music teachers played live jazz throughout—a nod to her roots as an accomplished cellist—and at one point her brother Gus also played the piano.

On Saturday, they married at the 150-year-old Watch Hill Chapel. Olivia wore a Dolce & Gabbana long-sleeve, crewneck crepe ball gown with a voluminous skirt and button-lined back. “I didn’t want it to exude sex in any way, shape, or form,” she says of the dress, which she wore with a 16-foot lace veil and 15-carat De Beers diamond earrings. “I wanted it to feel effortless and as if it’s complementing me, not overpowering me. There’s so much beauty and simplicity.” Her beauty, too, was pared back: She wore her hair down in a simple middle part and skipped mascara, lip liner, and eyebrow makeup. “I never felt more beautiful than when I was in my ceremony dress and under my veil—I really wanted the simplicity of each component to harmonize perfectly,” says Olivia. She walked down the aisle to Jeremiah Clarke’s trumpet voluntary, played by a string quartet that included her own mother. Her sisters, Sophia and Aurora, were her bridesmaids and also wore custom Dolce & Gabbana.

Olivia says she felt an overwhelming sense of peace during the ceremony. “Even with so many people in the room, it felt like it was just Christian and I,” she adds. The groom, however, was perhaps more nervous than he’d like to admit: “Christian blurted out ‘I do!’ within the first 30 seconds of the ceremony,” Olivia says. “The priest told him we weren’t quite there yet, and our family and friends had a great moment of laughter at his eagerness. As a bride, there’s no better feeling than your husband not being able to wait a second longer to marry you.” Finally, the time came. The couple said vows they wrote at the altar, which was adorned with white and green garden flowers.

After walking down the aisle to the cheers of their families and friends, the two drove back to Ocean House in a vintage Rolls-Royce.

A pre-dinner hour was held on a veranda overlooking the Atlantic Ocean. As golden hour began, guests entered the dinner tent through a floral archway by local florist Semia filled with garden roses, peonies, ranunculus, and oakleaf hydrangeas. The tables, meanwhile, were set with vintage silver floral vessels, antique garden urns, and bone china. “My dinner reception was a combination of old-school elegance and lush garden florals,” says Olivia. “It was really important to have a lot of greenery. I wanted the florals to be lush but garden style, as if they were organically growing.” The bride changed into her Dolce & Gabbana reception dress for the occasion: an off-shoulder high-waist chiffon gown with a handmade silk flower on the neckline.

Finally, under crystal chandeliers, everyone headed to the dance floor, where they stayed for hours. Olivia snuck off to change into her final look of the night: a silk bodysuit with a mini cage skirt—both adorned with handmade organza flowers— accessorized with tulle gloves and a satin flower choker. Guests showered the couple with biodegradable confetti as they made their exit to their supper-club-inspired after-party back at Ocean House.

A day after the wedding, Olivia and Christian say they’re still taking everything in. But what they predominantly feel is gratitude, both because of the weather (“We got so lucky,” the bride notes) and the amount of loved ones that came to Rhode Island. “Both Christian and I felt our wedding weekend starts our life together as a family,” Olivia says. “I wanted everything to feel intimate but also include the gravitas of the moment.”

Enjoying a moment together during their Welcome dinner at the Ocean House in Watch Hill, Rhode Island. Photo: Jose Villa

olivia culpo wedding

Cutting our cake. Photo: Jose Villa

Hit the dancefloor. Photo: Jose Villa

olivia culpo wedding

Changing into my custom Dolce & Gabbana after-party look. Photo: Jose Villa

Enjoying our siblings’ speeches. Photo: Jose Villa

olivia culpo wedding

Brooks Nader and Prince Constantine Alexios of Greece and Denmark. Photo: Jose Villa

olivia culpo wedding

Our first dance. Photo: Jose Villa

Our six-tier wedding cake by Confectionery Design included alternating tiers of vanilla sponge and red velvet cake. Photo: Jose Villa

olivia culpo wedding

Arriving to the dinner reception and being formally announced as Mr. and Mrs. McCaffrey. I’m in my custom Dolce & Gabbana reception gown. Photo: Jose Villa

The entrance to the dinner reception adorned with a lush floral archway of beautiful white and green florals including garden roses, peonies, ranunculus, and oak leaf hydrangea. Florals by Semia. Photo: Jose Villa

olivia culpo wedding

With our dog Oliver. Photo: Jose Villa

olivia culpo wedding

A playful moment with our nieces and nephew. Photo: Jose Villa

With our flower girls, page boy, and dog-of-honor. Photo: Jose Villa

olivia culpo wedding

We had a “Just Married” sign on the back of our vintage Rolls Royce. Photo: Jose Villa

Waving to everyone after our wedding ceremony. Photo: Jose Villa

olivia culpo wedding

Together in the back seat of a vintage 1957 Rolls Royce Silver Cloud. Photo: Jose Villa

olivia culpo wedding

Smiling under a custom-made floral archway by local Rhode Island florist Semia. Photo: Jose Villa

Exchanging vows we wrote for one another. Photo: Jose Villac

olivia culpo wedding

Walking down the aisle. Photo: Jose Villa

My nephew and page boy Remi walking the dog-of-honor, Oliver, down the aisle. Both in custom Doloris Petunia. Photo: Jose Villa

olivia culpo wedding

Taking wedding portraits at the historic Elms Mansion in Newport, Rhode Island. Photo: Jose Villa

olivia culpo wedding

In my custom Dolce & Gabbana wedding gown. Photo: Jose Villa

The groom in the final moments before the wedding ceremony commences. Photo: Jose Villa

olivia culpo wedding

Getting last minute touchups in Dolce & Gabbana makeup by makeup artist Mary Phillips, and hair by Dimitri Giannetos. Photo: Jose Villa

My niece and flower girl, Soleil, in a custom Doloris Petunia dress. Photo: Jose Villa

olivia culpo wedding

Sharing a laugh during speeches from both of our fathers. Photo: Jose Villa

olivia culpo wedding

An abundant charcuterie spread—a nod to my Italian roots. Photo: Jose Villa

Italian signs guiding guests towards the fun and festivities during the welcome dinner. Calligraphy by Haniya Calligraphy. Photo: Jose Villa

olivia culpo wedding

Sun setting over the historic Ocean House. Photo: Jose Villa

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