As someone who began attending the Met Gala in her teens, Ali Lebow knew that curating the perfect wardrobe would be her main priority when planning her wedding. “I love fashion so much that I knew that this is where I wanted to invest my time,” she tells Vogue. But first, of course, she would need to find the perfect person to spend the rest of her life with.
The Manhattan native met Brooklyn-born Jake Nidenberg at a friend’s apartment as the world was beginning to open up after COVID. “I hadn’t seen a man in seven months, so I was completely feral,” the TikTok brand strategist jokes. “He was way more considered and actually wanted to get to know me—to my dismay.” After three months as friends, Jake asked Ali out on a date. “When he made a move, we had built this foundation for us,” she says. A short period of “long-distance dating” between Manhattan and Brooklyn concluded with the couple moving in together in Boerum Hill. “My little Upper East Side self lives in Brooklyn with him and I love it so much,” Ali says.
Jake would later propose on the beach near her family home in East Hampton. Although Ali says the Booknook CFO can be a “math nerd,” Jake showed his “creative edge” by working with a jeweler to design her engagement ring himself. “He told me he went to the jeweler seven times and picked out every stone.”
That careful attention anticipated Ali’s own process of selecting all the looks for their New Year’s Eve wedding at the former Domino Sugar Factory in Brooklyn. The bride admits she did not have a particular “dream wedding dress” going in. “My goal was never to look classic or timeless, because I think that’s boring,” she explains. “I just wanted to hopefully create some things that felt different. It’s not going to be everyone’s cup of tea and I understand that.”
One of the first steps in building her wedding wardrobe was hiring bridal stylist Carrie Goldberg. “If I’m gonna put my money for this wedding literally anywhere, it’s going to be with her, because I just knew I needed a sounding board,” Ali says. The bride admits that some friends wondered why she would hire a stylist when she had such a strong sense of personal style and close ties to the fashion world. “I just see it as someone who can interpret my thoughts and share in my vision,” she says. “Even though I didn’t have a dream dress, I had a dream experience of creating something with someone I really admired.”
The final bespoke ceremony gown featured a halter neck, a tuxedo-inspired bodice with a mandarin collar, and a full skirt with tiered ruffles by Christopher John Rogers. Goldberg was the one who made the introduction. “It’s funny, because Christopher is so known for how he uses color and we designed an all-white dress together,” says Ali. “But I think it still has a playfulness as well as that structure and integrity that I was so drawn to from his designs.” The bride also admired the designer’s New York sensibility and personal dedication to his work. “I think he’s such an amazing talent,” she gushes. “Sometimes you work with a designer and you really only get them for the initial fitting and the final fitting. He’s on his hands and knees in every fitting. He’s the one sketching. He’s doing everything with his incredible partner, Shea.”
The gown had three sources of inspiration. The first was a hand-painted Oscar de la Renta gown with a mandarin collar and halter silhouette, owned by her grandmother. Ali joked that it would be the only thing she’d grab if her house were on fire. “I actually wore it to my first-ever Met Gala when I was 16, and saw Oscar de la Renta there before he passed away,” she recalls. “He stopped me in my tracks and said, ‘I need this dress for my archives.’” Ali called him the following week and admitted she couldn’t give up the vintage piece. “He laughed and was like, ‘Okay, I totally understand that. If you change your mind, let me know.’ Then he let me come into his office and try on other dresses to wear to prom. It was the highlight of my life, and my grandma came with me to that appointment. So this dress has been in my life for a long time.”
Her second source of inspiration was menswear. “I can’t remember how the idea for a tuxedo shirt came to mind, but Carrie and I were just talking about the elements of menswear we really admire and that was a detail I kept coming back to,” Ali says. “So when I was looking for designers, I was looking for someone who knew tailoring.” The third piece was a ruffled skirt that Rogers produced in his first mockup. “When Christopher drew up the sketches, I was like, ‘That’s 100 percent what I want to do.’ Those tiered ruffles just feel so iconic to him. I wanted it to be a fusion of both of us, so I felt like the top was very me and the bottom was very him. It still felt really unified.”
Ali met with Rogers and his team for five fittings to bring the custom look to life. “We spent a lot of time together and it was really nice,” she reflects. “I love how considered they were throughout the entire process.” While her mother joined her for some fittings, Ali kept what her dress would look like a secret from everyone else—including her fiancé, Jake. “But he actually kind of guessed, which was funny! He just knows me so well,” she says.
Since the wedding was held on New Year’s Eve, the bride also needed a look for ringing in 2026. “The creative brief for this after-party look was if a disco ball and a rainbow threw up,” she says. It ended up featuring a long, shimmering Rabanne dress and an archival silver Dries Van Noten coat. “I was so obsessed with that coat. The inspiration for that was tinsel,” says Ali. The bride reveals that Goldberg was able to source both pieces from a fashion closet just seven days ahead of the wedding.
The last part of Ali’s wardrobe was the vintage dress that her grandmother had worn to her own New Year’s wedding. (Ali’s mother had worn the dress as well.) “It’s amazing when you can feel this whole lineage of women behind you and repurpose clothing that they actually wore in those life moments,” the bride says. “I love that about clothes—how they can defy time. In my mind, I have a future flamboyant grandson who takes all my gowns. Anytime I’m shopping I think, would my grandchild in my brain want to wear this?”
Since Ali is about four inches taller than both her mother and grandmother, the dress unfortunately did not fit her off the hanger. “Once I knew I needed to alter it in some way, I was like, ‘Okay, let’s just go crazy.’ My grandma said, ‘Do whatever you want to it’ and gave me her blessing.” So Ali turned to Patricia Voto of One/Of to transform the gown. “Together, we came up with an idea to make it into a coat that went all the way to the ground and pants,” she explains. “At first I thought we would keep the original train. Then I thought: ‘I’m at Hometown Barbecue. What the fuck am I doing in a train?’”
As perfect as all the clothes for her wedding weekend turned out to be, the process of putting them together, and the relationships that she formed along the way, were a highlight of the whole experience. “When I look back at wedding planning, that’s what I think of,” Ali shares. “I think of all the people in the meetings and the work and the decisions and my grandma and everything that went into it. It just makes it that much more special.”
