Jake Stein, the president of Def Pictures, a film and theater production company founded by Russell Simmons, had just moved to Los Angeles from New York when he was invited to a group dinner by a friend. “It was not meant to be a setup at all,” says Isabel Roth, who is now a third-year law student at USC. “Jake was already in the car when my friend David came to pick me up that night. He got out to open the door for me, all gentleman-like, and we did this sort of awkward handshake. We ended up sitting across from each other at dinner where he proceeded to order a petite filet split between three men and five other things for ‘comedy.’ I immediately thought, ‘This goof is for me.’ I teased him incessantly, and he made me laugh all night. It felt like we had already known each other forever.”
Fast-forward four years, Jake popped the question on Christmas Eve at his family’s home on Martha’s Vineyard. “After dinner, we walked back to the guest cottage where we were sleeping that weekend, and when I opened the door, all I could see were hundreds of candles and flower petals,” remembers Isabel. “I didn’t even see the ring box sitting on the table. I was so surprised that my brain didn’t compute that this was the moment. He told me to close my eyes, and when I opened them, he was down on one knee with the most beautiful ring I’ve ever seen that he had been secretly designing with London-based jeweler Jessica McCormack for months! I screamed, we both started bawling, and then we texted Jake’s brother to come to the guesthouse and celebrate. He had secretly been sitting in the woods spying through the window so he came right in. We waited until the next morning to tell our families. That year, we did a joint family holiday so my dad and stepmother were there as well. We told them at breakfast on Christmas morning and then we all got in onesies and opened presents by the tree—it felt like a movie!”
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Both Isabel and Jake have always loved Italy—“especially the wine and pasta aspect of it,” says Isabel, laughing—and they wanted to create a unique destination experience for their guests. They knew traveling to Europe was a lot to ask of people, so it took some time for them to actually commit to a destination wedding, but eventually they decided to go for it. Ultimately, they couldn’t resist the idea of vacationing somewhere special with all of the people they love the most. “You really only get the opportunity to do that once in your life, if ever,” Isabel points out.
The couple’s wedding planner, Lisa Vorce, came up with the idea of Puglia, specifically Borgo Egnazia. She had visited the region several years before and had been dying to do an event there. “We trusted her implicitly and planned a last-minute trip the summer of 2016 to visit,” says Isabel. “We spent three days there and fell in love. The rest of the wedding aesthetic flowed easily from there. Borgo Egnazia is pure magic. The hotel feels centuries old and is designed after a typical Apulian village with a borgo (small town), corte (small hotel), and 24 expansive villas. Since the look is so unique, we really wanted to showcase the region’s authenticity throughout the weekend, which Lisa executed perfectly.”
Choosing the dress was a bit harder for the bride-to-be. “I didn’t even know where to go to try one on—I’m slightly challenged in this department, but Cynthia Cook Smith, of Cynthia Cook Brides, helped me find the perfect dress by Reem Acra,” explains the bride. “I flew to New York to try it on last November and knew right away it was the one. I just kept describing it as ‘me in a wedding dress.’ ” Isabel had a few more fittings in Los Angeles where she added some additional appliqué because the runway version of the dress was very sheer.
Philippe Tholimet did her hair for the rehearsal dinner and the wedding day. “He truly is a master,” says the bride. “Because he lives in London, we never did a trial. We actually never even discussed it, but I sent him a Pinterest board of the types of hair I’m generally into. I just sat down with wet hair that morning, he showed me a photo of a style he thought would be great for the dress, and I said, ‘Let’s do it!’ ” Isabel did her own makeup. “I love doing it—it relaxed me and removed any fear I had about not looking like myself on my wedding day.”
Just before the ceremony, Isabel’s mother-in-law and stepfather-in-law surprised her with a stunning antique Cartier bracelet from the 1920s. “It was my something old,” says Isabel. “As my something borrowed and something blue, I wore aquamarine Asprey earrings that my dad gave my stepmother when I was around 12 years old—and I distinctly remember wanting them so badly!”
The ceremony took place on a rooftop terrace with an expansive view of endless olive groves, Puglia’s rich red soil, and the Adriatic Sea. “I loved that the location had this natural grand entrance,” explains Isabel. “Our only concern beforehand was the wind, and it ended up being windy as hell, but we didn’t care.”
The bridal party processed up the aisle to Leon Bridges’s “River.” “I got chills listening to this song as I was waiting in this alcove with my dad before our walk,” says Isabel. “Right after my two little nieces did their flower girl duties, my dad and I made our way up the aisle to Van Morrison’s ‘Sweet Thing.’ My heart was pounding out of my chest during the entire walk, and my long Carolina Herrera veil got caught a few times on the stone behind me. I actually felt like one of those Looney Tunes cartoons when they fall in love and their heart beats, stretching their skin out of their chest, and you can hear the ‘thump-thump!’ ”
Once under the chuppah, Rabbi Leder from Wilshire Boulevard Temple performed the service. “He spoke words that I will remember and cherish for my lifetime,” says Isabel. “Jake and I said our own vows to each other. Writing our own vows was easily the most stressful part of the entire process for us, but Jake’s blew me away. I was all at once emotional, honored, and just plain old impressed by how beautiful they were. His mom had suggested that we write our own and looking back it was one of the best parts of the weekend.”
Guests relocated to Villa Padronale for dinner with dancing to follow at Borgo Egnazia’s beach club, Cala Masciola. “We served what probably is a very American interpretation of an Italian feast: caprese salad to start, a pasta course of penne all vodka—Jake’s favorite—and Puglian-style carbonara served family-style, and then a plated option of either steak or chicken Milanese. It was delicious!” says Isabel.
The father of the bride introduced the newlyweds for the first time as “Mr. and Mrs. Isabel and Jake Stein” and then gave a touching toast. “He sang a portion of Frank Sinatra’s ‘Soliloquy’ to me while Peter Cincotti played a beautiful white piano in the corner of the tent,” remembers Isabel. “I have never heard my dad sing in my entire life, so I was completely shocked and couldn’t stop crying. A little while later, my brother, Josh, and Jake’s brother, Ben, gave two beautiful toasts that made me cry all over again. There were a lot of tears that day.”
When dinner ended, guests went down to the beach club for dancing and a surprise fireworks display. The bride changed into a John Galliano white dress cut on the bias for her first dance with Jake, and then again, a little later in the evening, into a funky custom white sequin jumpsuit. “Lisa and her team executed my vision for the after-party so well,” notes Isabel. “I wanted it to feel like an exotic masquerade ball so she hung tiny little candles down from the ceiling along with stars and ornate Moroccan lanterns, and covered the perimeter of the dance floor with layered Moroccan and Persian rugs. We handed out these sexy little masks in silver and black for all our guests to wear while dancing.” DJ Sam French had everyone dancing all night—“quite literally . . . I think we danced until 7:00 a.m.,” says Isabel. “He also put up with all of my odd requests!” Afterward, Isabel and Jake went back to their room, ordered some pasta, and watched the sun rise on the rooftop of their villa.
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