A Sophisticated Black-Tie Wedding in San Francisco

Hailey Stone and Ben Sperry met through mutual friends at a birthday party in San Francisco in August 2017. Two years later on November 9, 2019, Ben proposed at another birthday party. This one was for his bride-to-be. “Ben proposed on Hailey’s 30th birthday,” the couple shares. “He had an amazing party planned at our favorite place in Sausalito, Le Garage, with all our closest friends and family. He popped the question right before guests arrived and Hailey’s ‘birthday’ became the most beautiful engagement celebration.”

Navigating COVID was the hardest part of wedding planning, the couple shares. They originally planned a winter wedding at San Francisco City Hall, but pivoted to October 2021 at St. Vincent’s School for Boys. “Hailey’s family has been coming to St. Vincent’s for many years; her mother volunteers there and they have grown to absolutely love it,” the couple shares.

“The grounds are so special and historic. We loved the charm and how meaningful the venue was to us, while also providing one location where our guests could arrive and enjoy the night without worrying about a venue change.” They continue: “Our vision was to create a sophisticated black-tie event that felt meaningful and allowed guests to have a great time. We didn’t want a stuffy wedding, that is not us as a couple. We wanted something beautiful and elegant but, most importantly, relaxed and fun.”

They turned to a very special partner to design the event: Hailey’s dad, Mike Stone. He and his creative team at Stone Living, a contracting and home design firm in San Rafael, brought the couple’s grand vision to life. “My dad did everything from the design of the entire weekend to the floral arrangements; he was the brains behind the entire wedding operation,” Hailey says. “He knows Ben and I so well that we shared a common vision the entire time.”

Keep scrolling to explore all the sophisticated details and unique touches of their October 9, 2021, wedding, planned by Cinthy Moreau Walsh of A Touch of Grace Events and photographed by Larissa Cleveland.

The party got started long before the wedding day. “The weekend was Fleet Week in San Francisco, one of our favorite weekends,” the couple shares. “Hailey’s brothers chartered a boat to watch the air show for all the groomsmen, uncles, and cousins, which was an amazing way to kick off the weekend. We had our rehearsal dinner at our favorite local spot in downtown Tiburon, Salt & Pepper, and our welcome party at Sam’s Anchor Cafe—both places we frequent very often.” For the rehearsal, Hailey combined pieces from two of her favorite designers, Nadine Merabi and Victoria Chapman, for a chic suited look. 

Though she tapped Sherrie Long for her wedding-day makeup, “I actually ended up doing my own hair!” Hailey remembers. “It was important for me to feel like myself. I knew I wanted my hair completely down, so it was an easy task.” 

“I’m very particular when it comes to fashion,” Hailey admits. “My dress was a true reflection of my style. I chose a Ines Di Santo dress and worked directly with Ines and the amazing crew at Bridal Galleria. We started with a muslin design and worked until it was perfection!”

She paired the gown with Amina Muaddi earrings and Jimmy Choo heels. “I wore two diamond tennis bracelets. One was a gift from my Grandma Marie on my 21st birthday, and the other was a gift from my mother- and father-in-law at our rehearsal dinner. Both belonged to women in our families before they were passed on to me. They both mean so much to me.”

One final touch? “At the end, we decided on the petticoat cape that wrapped around my forearms, rather than a veil,” shares the bride.

She paired the gown with Amina Muaddi earrings and Jimmy Choo heels. “I wore two diamond tennis bracelets. One was a gift from my Grandma Marie on my 21st birthday, and the other was a gift from my mother- and father-in-law at our rehearsal dinner. Both belonged to women in our families before they were passed on to me. They both mean so much to me.”

“I wanted my bridesmaids to feel confident and sexy, while also being appropriate for a church wedding,” Hailey says. “One of my favorite designers, Solace London, made all the bridesmaid dresses and the girls got to choose their favorite dress that suited their own personal style.” She always wanted to make sure they could rewear the gowns. “You can never have too many black dresses, and I knew they would appreciate the new additions to their wardrobes!”

A trio of flower girls—Hailey and Ben’s nieces—wore black dresses to match the bridal party. Ring bearers, meanwhile, wore black shorts and suspenders with Sperry boat shoes, a fitting tribute to the couple’s last name. Hailey carried a simple but elegant bouquet of white peonies and Lily of the Valley.

The couple opted not to do a first look; “We wanted the first time we saw each other to be in the church,” Hailey shares. Her dad accompanied her the aisle to an acoustic version of “My Girl.”

Family friend Archbishop Tom Daly married the couple. “We wrote down our own vows about why we chose to spend the rest of our lives with one another, and Bishop Daly read them during our wedding ceremony,” the couple explains. “Our godmothers both did readings, as well as our three siblings.” 

Bill Withers’ “Lovely Day” played as the newlyweds exited the ceremony. “Walking out of the church as husband and wife—the moment after we were officially married—was a very special highlight,” they remember. “Our friends and family were so excited. It felt like a concert; people were cheering and celebrating with us from that moment on. The smiles on our faces didn’t fade for weeks after that moment!”  

Ben wore a Hall Madden tuxedo and his father’s cufflinks for the big day. Groomsmen matched him in classic tailored tuxes with loafers and no socks—and a personal touch: “Each groomsmen picked out their own custom lining for their tuxes,” the couple shares. 

Father of the bride Mike Stone and his creative team executed all the florals, bringing the couple’s black, white, and gold vision to life in epic fashion underneath a tent in the courtyard at St. Vincent’s. “Our linens were originally chosen for a winter wedding at city hall, but they fit perfectly at St. Vincent’s, too,” Hailey says. “They were cream and black velvet.” 

“The moment that stands out the most to us was when we entered the reception area. We had not seen it until that moment,” the couple recalls. They were introduced by Hailey’s oldest brother, who served as emcee for the night. “From the moment we walked out, we couldn’t believe our eyes! The courtyard had been transformed. Everyone was in such amazing spirits, nobody wanted to be seated!”

“We had many personal touches,” Hailey says. “The most memorable was that Ben and I hand-wrote notes with photos for each guest as their place setting. While this was a time-consuming task,”—they had 240 guests!—“it was so amazing to watch everyone open their personalized note and realize we had taken the time to thank every single person for being there.”

As they listened to heartfelt speeches, guests tucked into dinner, which began with barbecued Hog Island oysters. “My Uncle George took us wine wasting and we chose our favorite white wine, Taylor Family Vineyards chardonnay, which he generously gifted us for our dinner service,” Hailey shares. 

“Our first dance was to Bruno Mars,” Hailey says. “We wanted to immediately get the party started for our guests.” Speaking of starting the party, nothing does it quite like an outfit change. Hailey swapped her gown for a disco-inspired gold jumpsuit by Nadine Merabi, and her father surprised Ben with a tailored white dinner jacket to change into at the same time. “It was such a special moment for us,” they remember. “We had so much fun dancing together and kicking off the party.”

Rather than two separate parent dances, Hailey and her dad and Ben and his mom hit the dance floor all together. “We danced to ‘I Can’t Help Myself (Sugar Pie, Honey Bunch)’ and the four of us shared the song,” Hailey says. “We wanted to feel like a family, and the first dances were a great way to do that!”

The live band, Downbeat Agency’s Gold Standard, had everyone on the floor. “The energy and dance party was one for the books,” Hailey remembers. “If you surround yourself with the right team—your soon-to-be husband or wife, family, planners, wedding party, and vendors—it will be the most amazing experience!” Her takeaway for other couples? “Take time over the weekend to spend a moment together and appreciate all the love you have as a couple,” she says. “It truly goes so fast and is the most amazing weekend of your life.”