Danielle Calleja, an investor relations professional, and Matthew Winger, a public and private market investor, met at work. “We knew each other for a little over a year before finally admitting that we liked each other. We are forever indebted to very good friends of ours, who, when they realized we were both single, brought us together,” Danielle says. After two-and-a-half years of dating, he proposed on a ski trip with friends in Aspen on her birthday!
“Matt pulled off a surprise proposal, even though I was very direct about wanting to marry him (and even had some say in designing my ring!),” she says. On a last ski run alone before lunch, Danielle was ahead of him, when he called out, “Wait!” and complained of foot pain. “I protested and nudged him to ski back to the lift (and our friends), but he insisted I climb uphill (in my skis!) and help him with his boot.” Under the guise of loosening his boot, he got on one knee and took the ring out from his pocket.
For their wedding, Napa was a natural choice, as the bride’s parents had fallen in love with the place early on in their marriage, and her family has since spent a lot of time in the area. Danielle and Matt wanted their reception to feel like a giant dinner party, and prioritized the food, wine, and ambiance during the planning process. To accommodate both the ceremony and festivities in a single outdoor space, they found the Vintner’s Glen at Meadowood Napa Valley. “Anna Hoffman of Loop Flowers designed the florals— ‘fluffy, romantic blooms combined with seasonal texture, vines, and foliage in earthy ceramic bowls’—which created the perfect, classic garden atmosphere,” the bride explains. To help plan everything, the couple hired Alexis Alexander of Cole Drake Events, and Danielle’s mother, who works in the wedding invitation businesses, was also a phenomenal guide.
To kick off the weekend, Matt’s parents hosted a welcome pasta and wine dinner at Paraduxx on Thursday night. Cynthia Cook Smith, who helped style the bride for all her events, picked out a Johanna Ortiz silk, rose-print gown for the evening, and Danielle took a cue from the look book and paired the dress with a black grosgrain ribbon tied around her waist. The next morning, her aunt and uncle threw a picnic catered by Meadowood at Odette Estate. For this occasion, the bride opted for a Cult Gaia cream seersucker number with Gianvito Rossi block heels.
When it came to picking out “the dress,” Danielle unexpectedly fell in love with bridal shopping and tried on more dresses than she’d care to admit. “The one” was ultimately a Naeem Khan embroidered creation. “My mom likes to remind me that she picked out this dress. She asked me to indulge her by trying it on. It was unlike anything I’d considered, but when I walked out of the dressing room, my mother, sister, Cynthia, and I all agreed that it was perfect,” the bride says. To walk down the aisle, she paired her gown with blush suede Aquazzura shoes, and she trusted Sherrie Long to create a dewy, natural makeup and hair look.
For his wedding day look, the groom worked with Pepi Bertini in Coral Gables to create a custom outfit. “Although I initially imagined Matt in a simple and elegant suit and tie, he was adamant about getting married in a tuxedo. I’m so glad he did!” Danielle says.
On May 4th, 2019, with sunny skies, the bride processed down the aisle, lined with white florals, dogwood, and ferns toward the birch chuppah. The trees surrounding the glen had bloomed the day before, so the atmosphere was particularly secret garden-esque. Rabbi Lee Bycel, author of Refugees in America, officiated the Jewish service, and in the months leading up to the wedding, he made Danielle, who grew up Catholic, feel so welcomed, as they worked to customize the ceremony. After sharing their first kiss as husband and wife, the two headed back up the aisle to “their song,” “My Girl,” played by the Brian Moran Trio.
At the reception, the seated dinner catered to all the guests’ dietary preferences, and Alexis and designer Meredith Law printed individualized menus for each person. The delicious meal consisted of Maine lobster, a sweet pea agnolotti, and a choice of red snapper, grilled tenderloin, or Maitake mushrooms, with wine pairings for each course. For dessert, their wedding cake was a Meyer lemon, lavender, and strawberry cake with local honey buttercream by Susan Williams from Cake Bloom. “Matt and I took home the beautiful miniature version she made us with the intention of freezing it and enjoying it on our anniversary…. but couldn’t wait a whole year and devoured it within two days of getting back home. I didn’t know a wedding cake could taste so good,” the bride says.
For an evening ending with dancing, Danielle changed into a Givenchy pearl-detail dress, and for the after-party, her third outfit consisted smartly of a light cotton hoodie and soft sweatpants. Since the bride’s guilty pleasure is a great dive bar, the remaining group headed to Anna’s Cantina in St. Helena.