When two entrepreneurs’ lives collide, magic can be made. That was certainly the case—times two—for Cassandra DiMicco and Matthew Hoyle, who became partners in both business and life after their paths first crossed in 2017.
“We met in April 2017 at the Coachella afterparty Neon Carnival,” says Cass, who you probably know best as the chic and ever-fashionable influencer behind @cassdimicco. “We crossed paths, instantly started talking, and both happened to be living in New York City. We started dating when we both returned home.”
It was a love connection from the jump, and became even more: The pair got engaged in November 2019 at Amangiri in the Utah desert, and around the same time launched Aureum Collective, a line of luxury jewelry made for the everyday. (The label just celebrated its second anniversary with a must-shop collection that includes a handful of pieces Cass donned on her big day.)
After Cass said yes, the couple got to wedding planning right away. “Our original wedding was set to be a big party in Marrakech. But after COVID hit, we reevaluated and decided we wanted to do a family trip instead,” Cass says. “Matt and I have been very passionate about wine lately, so we decided to change our wedding plans to center around that.” They booked a venue site unseen— Castello Di Vicarello in Tuscany, Italy—to host their welcome party, rehearsal dinner, and wedding.
“It looked beautiful, and we wanted the excitement during our wedding of visiting a new place for the first time,” shares the couple, who are avid travelers. "Sure, it made planning somewhat difficult, but it was worth the wait. It was hard to imagine where each dinner would take place, as well as the reception and ceremony,” Cass admits. “Figuring out how to make each night feel different was hard to plan without ever visiting, but [the venue’s team] really helped guide us.”
Luckily, once they’d locked in their venue and decided on the small guest count, planning was “fairly easy,” Cass shares, adding gratefully: “I’m not much of a planner so I was glad it all went seamlessly.” She continues, “I really wanted the location to be the focal point and the flowers to be an added bonus. I wanted everything to be simple, classic, elegant, and not too over-the-top."
The ceremony and reception were really just icing on the cake to an incredible trip through Italy. “Our wedding was more of a big family vacation; we went from Rome to Florence to Tuscany to Venice,” Cass says. “We really wanted our wedding to be one long, amazing experience together, rather than a one-day affair. I think that helped ease a bit of the pressure of everything needing to be perfect for the actual wedding day—because no matter what happened that day, I already had such an amazing trip leading up to it.”
“I loved how private and romantic the hotel was,” Cass says of Castello Di Vicarello. “The views, décor, food—everything was breathtaking. The staff was also unbelievably warm and accommodating. They did everything possible to make the day perfect.”
Castello Di Vicarello was not only a beautiful venue, but it was also full of character and charm. It even has its own property dog, aptly named Uva (meaning “wine” in Italian). “She was such an angel and made us so happy when we were missing our own dog, Pepperoni,” Cass says. Groom-to-be Matthew gave Uva a pat before the welcome party, two nights before the big day.
The welcome dinner look was something I stumbled upon that felt so bridal, but not as expected.
“The welcome dinner look was something I stumbled upon that felt so bridal, but not as expected,” Cass says of her feathered set from Valentino’s Fall 2020 collection. “I loved that it was white and blue, and overall just a fun, comfortable look.” She paired it with wide gold hoops and a chain necklace from Aureum Collective, and a bridal-inspired Chanel bag.
The next evening, October 6, was Cass and Matthew’s rehearsal dinner—and an excuse for another stellar look from the bride, who rocked a Celine dress and pearl Jimmy Choo platforms. “Even though it was black on the lower half, the over-the-top ruffle detail still felt bridal,” she says of her choice. “I added pearl earrings, hair clips, and shoes. Overall, I really wanted to have fun and take more of a risk with the looks for the welcome party and rehearsal, and keep my wedding-day look classic.”
The easiest part of the planning process? “Picking the food!” Cass says. “For our rehearsal dinner, we had a full truffle menu, which I was so excited they offered.” During dinner, the bride’s mother, groom’s mother, and groom’s sisters all delivered heartfelt speeches.
Cass’s advice to brides and grooms: Take ALL the photos. “I wish I took more photos and videos myself, or had my family take more,” she says. “Of course, we rely on our photographers and videographers, but to capture the more intimate moments.” This sweet scene, captured by photographer Lisa Poggi, is a perfect example.
All of the wedding florals were white and ivory—including the petals handed out in monogrammed cups to be tossed after “I do.” “At first, I was going to try to find a color scheme I loved—but I realized [with] planning from another country, white and ivory was a safe, timeless bet,” Cass says. For her personal arrangement, “I went with a small bouquet of white roses with short stems. I didn’t want anything too large to take away from my dress.” The groom and father of the bride also wore rose boutonnieres.
“I have a lot of hair and because my dress was so embellished, I wanted [it] out of my face and sleek. But, I don’t love how my hair looks fully pulled back,” Cass says. “So half up, half down it was! I left a small piece of hair from my bangs out, and my overall hair was brushed-out curls, kind of like a Hollywood wave. I loved how it turned out!”
The bride opted for an opaque nude color on her fingernails and spritzed on Tom Ford’s Ombré Leather perfume. As for makeup, “I kept it very simple, glowy, natural,” Cass shares. “We did a few corner lashes to make my eyes pop, and bronze shadow.”
“My shoes were Stuart Weitzman, a brand I’ve loved and have been working with for years," Cass says. "I even wore Stuart Weitzman on my sweet 16!” For the day, she put her own custom spin on the platform style. “I worked with a designer from their team to add the exclusive pearl and stone embellishments to the strap. Because my dress was so detailed, I wanted to keep the shoe simple, but add a touch of sparkle.”
The second I put it on, I felt like a princess.
Cass’s long-sleeve lace couture gown by Berta was the first dress she tried on. “The second I put it on, I felt like a princess,” she says. “Both of my parents joined me and they both knew it was the one, too. I bought it in 2019 and, many changed plans later, I still loved it.” She paired the look with self-designed earrings from her jewelry brand, Aureum Collective. “Matt and I have worked so hard building the brand together that it only felt right to have a special pair of Aureum earrings for my wedding day. They just dropped last week for our two-year anniversary collection. I love that I can wear them after our wedding, too, with a casual outfit or for a dinner date. They will now always hold a special meaning.”
The bride and photographer made the windy day work in their favor. “My veil was a long English tulle veil that I think complemented my dress so well, without taking anything away from it," shares Cass. "It was constantly blowing in the wind, which made for some amazing editorial shots; the light airy fabric is perfect for that effect.”
Meanwhile, Matthew donned a white tuxedo jacket from Brioni, paired with a Cesare Attolini shirt and black bowtie. “Because everyone was in all black, we loved the look of Matt wearing a white jacket,” Cass says. He finished his look with a spritz of Tom Ford Tobacco Vanille.
The scenic Tuscan landscape set the stage their ceremony. “Because we were walking through grass, we had a white runner so that my heels wouldn’t get stuck. Plus, I think it makes for a beautiful walkway,” Cass says. The wind also contributed to the look of the day. "We had candles and flower petals leading up to the arch that needed to be placed just moments before the ceremony so they wouldn’t fly away."
"I really wanted our floral arch to be unique, so instead of a full arch we added material that blew in the wind beautifully," explains the bride. "Plus, I loved how it didn’t completely block the view; I loved the balance between flowers, the Tuscan fields, and airy material. Tuscany Flowers absolutely blew me away—they did such an amazing job beyond my expectations.”
As Cass’s father walked her down the aisle, the sound of strings—provided by Kaleydo—wafted in the wind.
Cass and Matt each wrote their own vows for the ceremony. “That was very special for both of us," notes Cass. "A lot of crying!”
When the ceremony was over, the string trio took up “Can’t Help Falling in Love” as the newlyweds recessed down the aisle, guests throwing white rose petals in celebration.
The beautiful Tuscan wedding day was truly the perfect time and place for the couple to say "I do." "All week, every time I checked my phone it said there was a storm coming during our wedding. I was so stressed,” Cass remembers. “On the wedding day it never actually rained, which I was so grateful for.”
“Because we had such a small wedding we didn’t technically have a bridal party—basically everyone was in the bridal party!” Cass says. “Even though it was an intimate wedding, we wanted it to be black-tie and for everyone to get really dressed up. Matt and I love getting dressed up so that felt very us.”
Despite no official dress code, everyone showed up wearing black for the day. "This was actually unplanned, but everyone loves an all-black look and it’s the easiest to coordinate, so we just went with it," shares the bride.
“It was very important for Matt and I’s first look to be [while I was] walking down the aisle, so after the ceremony is when we all took photos,” Cass says. The couple traversed the grounds of the property to capture some epic shots.
Guests noshed on classic Italian charcuterie before sitting down at the lovely cocktail reception table. “I was set on having the dinner between the cypress trees, overlooking the fields,” Cass says. “I wanted full flowers through the middle of the table and then some on the floor to give the look of them cascading onto the grass.” Tuscany Flowers delivered, keeping with the all-white vibe and adding greenery.
Since the couple love wine, it was a highlight of their menu. ”We visited Antinori vineyard before [the wedding] and bought bottles of 2010 and 2015 Solaia,” Cass says of the wine pairing. “Castello Di Vicarello also has a house signature wine that was amazing.”
I’m so happy I had a small, intimate wedding. The pro is getting to spend the entire night with your husband.
“I’m so happy I had a small, intimate wedding,” Cass shares. ”The pro is getting to spend the entire night with your husband, because you’re not spending a lot of time making the rounds catching up with a lot of different guests.” The newlyweds soaked up all the joy as they snapped more portraits.
“Once it got darker and a little chillier, we moved inside for dinner,” Cass says. The meal? An Italian trifecta consisting of Caprese salad, tortelli ricotta, and Florentine steak. The bride and groom’s fathers and Matthew’s sister’s fiancé gave toasts while guests dined.
The guest count was small, but the love was felt far and wide. “Our family put together an amazing video from some of our best friends and family from home, saying congratulations and sending their love,” Cass remembers. “Of course I instantly teared up—I was not expecting that at all.”
After playing during the ceremony and cocktail hour, the strings retired, only to be replaced by an energetic DJ “playing a mix of old and new music,” Cass says. The party got going underneath a tent on the property grounds outfitted with a dark hardwood dance floor and bar. (Of course, pup Uva made an appearance.)
The bride changed into a stunner by CD Greene for the party portion of the night. The newlyweds danced to “Truly Madly Deeply” by Yoke Lore, and the bride and her father chose “I Loved Her First” by Heartland for their dance.
“Even though we only had 10 guests total, everyone was ready to party and brought the fun,” Cass remembers. “I’m so lucky to have a fun family with a lot of different personalities, so there was never a dull moment. Everyone brought the energy!”
“After the wedding, we headed to Venice, the last stop of our trip,” Cass says. “We stayed at the Aman Venice and had some amazing meals there.” It was the perfect bookend to their love story, too. Aman Venice is actually a sister property to Amangiri, where Matthew proposed. But the story isn’t over, of course. “This wasn’t our formal honeymoon,” Cass shares. “We will probably take another big romantic trip somewhere else soon.”
Ultimately, the wedding was everything the couple could have dreamt for, despite not being their original plan. The bride reminisces, “We spent so much quality time as a family, all danced together, and had a lot of laughs."
Venue Castello Di Vicarello
Bridal Designer Berta Couture
Bridal Salon L’Fay Bridal
Jewelry Aureum Collective
Bride’s Shoes Stuart Weitzman
Hair and Makeup Lara Navarrini
Officiant Alessio the Celebrant
Engagement Ring Delage Jewelers
Wedding Bands Miamira
Floral Design Tuscany Flowers
Catering Castello Di Vicarello
Videography Waterfall Visuals
Photography Lisa Poggi