Celebrity stylist Danielle O’Connell and Brian Sherlock have been in each other’s lives for 15 years. The two met in high school, went on to attend the same university, and remained friends even as life took them in different directions. “Can you believe we ended up with our high school crush?” they now joke. After years of unexpected encounters, phone calls, and showing up for each other’s milestones, they finally began dating.

Brian, however, had already made up his mind. He picked out Danielle’s engagement ring before they were officially together and proposed six months into their relationship, just before her 30th birthday. At his family’s home in Delray Beach, Florida, he invited her to watch the sunset in their favorite backyard spot. “He got down on one knee, and I dropped down with him!” Danielle remembers.

For their August 29, 2026 wedding, the couple chose Wildflower Farms in New York’s Hudson Valley. Just 90 minutes from Manhattan, the property offered the feeling of a destination wedding without traveling far from home. With all guests staying on-site, Danielle and Brian envisioned a weekend of celebrations, each with its own identity. The date was meaningful, too: They married on Danielle’s grandparents’ wedding anniversary.

Working with planner Mudari Creative, Danielle approached the design much as she would a fashion project. As a celebrity stylist and co-founder of Danielle & Alix, she wanted her wardrobe and the surrounding environment to feel connected. “I knew I wanted drapery to be a focus throughout each event, creating a thread that tied the weekend together and connected back to each of my looks,” she explains.

Ten looks, to be exact.

The weekend began with Danielle welcoming guests in an Alaïa two-piece set and boots, followed by an intimate rehearsal dinner for 24 guests among the trees. Here, she collaborated with bridal designer Seline Meisler on a custom four-piece ensemble inspired by the table itself: a runner made from vintage lace sourced around the world. The collected textures appeared in both her look and the tablescape, down to miniature lace aprons on the wine bottles. Staff wore custom Sherlock aprons throughout the weekend, while Minted created the rehearsal and welcome stationery.

For the welcome party, Danielle changed into Liz Martinez, choosing a look that reminded her of Wildflower Farms’ florals and landscape. The evening took place in the barn, where pizza ovens, pasta stations, and a circular wooden bar topped with flowers set a relaxed tone. A Rolling Stones-inspired playlist accompanied dinner before guests moved outside for s’mores and a custom photo booth.

On the wedding morning, Danielle wore two Chloé looks: first, a playful pajama-inspired set, followed by a romantic open-back dress. Hair stylist Dina DiPietro and makeup artist Jami Messuri created her beauty looks, with Danielle choosing to let each day’s mood guide the direction rather than planning everything in advance.

Her ceremony dress came together surprisingly late. Just two months before the wedding, Danielle discovered SEPT’s newly debuted collection and worked directly with designer Sarah to customize Gown No. 6 with bespoke sleeves and Veil No. 2. She became the first bride to wear two dresses from the collection. “I had never experienced that feeling of ‘when you know, you know’ until I tried this one on,” she says.

She finished the look with Jimmy Choo shoes and diamonds from Brilliant Earth, a brand she had worked with throughout her styling career and which had also created her engagement ring. Brian wore Boss and Santoni throughout the weekend, a nod to Danielle’s early career working in celebrity relations at Boss. His wedding band was especially meaningful: a gift from his father, who passed down his own ring to Brian, his only son.

Rather than a traditional aisle, Danielle made a long entrance through the trees. After riding with her father in a golf cart to the beginning of the trail, she walked toward Brian and their guests, eventually emerging from the trees. “It wasn’t until I turned the tree line and saw Brian and our guests far in the distance that I gasped and it all hit me,” she remembers.

Brian’s eldest sister officiated, and the couple exchanged personal vows before their 82 guests. Drapery by Tina Mamkegh was woven through the trees and chairs, while florals by Wild & Birch complemented the natural surroundings. Brian’s three sisters made up Danielle’s bridal party, wearing individually selected dresses by Zimmermann, Ance Gria, and Maria Lucia Hohan.

Photographer Jack Henry and videographer Karli Anne Films documented the celebration, with Follow The Bride capturing additional social content throughout the weekend.

Cocktail hour centered on a candlelit baby grand piano on the Great Porch, with fabric spilling around it. Inside, two long tables were dressed with cascading flowers, Sferra napkins, Zara Home plates, and custom wooden-and-linen menus by Off The Aisle, each personalized with a guest’s name to double as a seating card.

The couple entered the reception to the Rolling Stones’ “Miss You” before their first dance to “Stargazing.” Dinner featured a four-course menu, followed by red velvet, vanilla funfetti, and chocolate cakes from Miss Macs, the bakery responsible for Danielle’s birthday cakes for years. Later, the maid of honor and best man spontaneously began playing piano and harmonica together, drawing guests into a sing-along around the outdoor piano.

After the first dance, Danielle changed into SEPT Gown No. 35, a more sculpted silhouette with a lace bodice that referenced her ceremony veil. But the most unexpected fashion moment was still to come.

For the after-party, she chose vintage Dolce & Gabbana from Spring 2010. “Wearing a tank to your after-party? Absolutely!” she says. She traded her more traditional bridal jewelry for statement diamonds from With Clarity, layering approximately 92 carats for the occasion.

The newlyweds then invited guests into “Club Shirley,” a speakeasy-inspired after-party named in honor of their shared last name, Sherlock. The Stamp Studio created custom signage and elements for the space, which featured neon, cherries, a jukebox, custom merchandise, and dirty Shirley cocktails. DJ Shaun Pazel kept everyone dancing until 2 a.m.

The following day called for one final look: fringe by Isabel Marant. After a weekend in which every outfit had been considered alongside its setting, Danielle's last choice was refreshingly simple. “I simply needed something with fringe!”