Tennis player Caroline Wozniacki and former professional basketball player David Lee are married! The happy couple recited their vows in front of 120 family and friends at Castiglion del Bosco in Italy. The intimate ceremony was the culmination of a weekend that was all about understated elegance in a setting straight out of a fairytale, with a flawless wedding wardrobe to boot—the highlight of which was the bride’s Oscar de la Renta gown, embroidered with Lyon lace and worn with a classic cathedral-length tulle veil.
But way before her dress fittings at Oscar de la Renta—documented here—and an epic walk down a 262-foot-long aisle bisecting the town square at Castiglion del Bosco, there was the meet-cute in Miami that started everything. Caroline first crossed paths with David there three and a half years ago. “We met through a mutual friend of ours,” she recalls. They all went out for a group dinner and the two hit it off immediately. After a little more than two years of dating, he proposed with an 8.88 carat—eight is her lucky number—diamond engagement ring in Bora Bora in November of 2017.
“I had just won Singapore, the last event of the year, and we went to Bora Bora on vacation, and he said that he didn’t know when he was going to propose, but that he had the ring, and it’s burning in my bag, it’s burning in my pocket, so I need to do it,” she remembers. “He set up this sunset cruise with a dinner on a private island, and on the cruise, there was this guy with a small guitar playing music and all of a sudden, I saw David panic, and he goes to his backpack and starts searching for something, and I said: ‘What’s happening?!’ and he’s like, ‘Oh, nothing!’ Then, he grabs the box with the ring and he goes down on one knee, and he proposes. Whatever he said, I don’t remember—I was kind of in shock. When I panic, I start laughing, and I wasn’t expecting it so I started laughing and said, ‘Of course, yes.’ And he was like, ’Is that a yes?’ And I was like: ‘Yes!’ It was right at sunset, and it was beautiful!”
After the surprise of the engagement had sunken in, Caroline “phoned a friend,” so to speak. “I emailed Anna [Wintour] and said I needed help,” laughs last year’s Australian Open winner. “Anna kindly said, ‘I would love to help you—what would you like?’” Caroline remembers. “So I sent her inspiration photos, and she suggested I come to her office so we could talk about it. So I went in, and we discussed ideas.”
Caroline knew she wanted a look that was equal parts romantic and girly, and ultimately turned to Oscar de la Renta co-creative directors Laura Kim and Fernando Garcia to create her dream dress for her and David’s destination wedding. “Caroline reached out to us, and we showed her a couple of silhouettes,” Fernando remembers. “Then she said, ‘I hate everything! Restart! Just kidding!” he jokes. “Actually, she was very clear that she wanted something lace-oriented with structure. She ultimately came in the first time with two friends and was FaceTiming with her mom.” The bride-to-be had done her homework—she’d gone through the bridal lookbooks, and the team at Oscar de la Renta had all of her selected gowns ready for her. “She tried them all on—slim-fitted silhouettes, ballgowns, lots of different types. She tried a couple of lace looks, and we landed on this quite quickly,” Fernando adds. A few adjustments were made to the strapless V-neckline so that it worked perfectly with Caroline’s body, and custom Jimmy Choo heels were commissioned.
The couple initially looked at venues in the South of France before switching gears to Italy. “We love Italy—we’ve had the best vacations there,” Caroline explains. “We love the food, the wine, everything, so we started looking at Italy and found this place that’s absolutely amazing.” The place: Rosewood Castiglion del Bosco Hotel, which was the suggestion of the couple’s event planner Alex Fitzgibbons of Fait Accompli, is one of the oldest estates in Tuscany and also where Kate Upton and Justin Verlander married. Founded by Massimo and Chiara Ferragamo, the property boasts around 5,000 acres but has just 23 suites and 11 luxury villas, making it feel like a secluded enclave nestled in the hills outside of Florence. The quintessential Tuscan landscape—fields covered in lavender and stone pathways lined with Italian cypress tress—and the sereneness of the estate called for an ethereal-feeling dress, and the team at Oscar de la Renta delivered.
At 6 p.m. on Saturday, June 15—one of the days of the year with the most sunlight, according to the bride—Caroline, escorted by her father, walked down the aisle wearing her custom-ordered Oscar de la Renta fern and floral lace-embroidered gown with a classic cathedral-length tulle veil. She and David said their vows before guests that included Serena Williams (who served as a bridesmaid) and Alexis Ohanian, Milwaukee Bucks NBA player Pau Gasol, Sacramento Kings NBA player Harrison Barnes, TV host and former NFL player Jesse Palmer, and pro tennis player Angelique Kerber—and the couple was pronounced husband and wife at that perfect moment in Italy when the light looked the most magical.