Wedding of the Day
Real Weddings

Annie Lawless’s Spectacular Wedding in Positano

This over-the-top celebration was straight out of a fairytale.

Photo by Gianni di Natale

Every year for her birthday, Annie Lawless, CEO of Lawless Beauty, and her now-husband Jeffrey Jacobs take a road trip up the California coast, from San Diego to Santa Barbara to Big Sur to Napa. “My favorite stop during the trip is at Post Ranch Inn in Big Sur, so in 2016, we arranged it so we’d check in right on my birthday,” says Annie. As she and Jeff were getting ready to go to dinner, he ordered a bottle of rosé and suggested the pair watch the sunset on their balcony. “I thought nothing of it—it was my birthday, after all,” Annie remembers. Jeff asked her to close her eyes while he went to get her present, and when she opened them again, he was standing in front of her, telling her how much she means to him. “I didn’t realize he was proposing until he got down on one knee,” she says. “It was a complete surprise!”

Annie wanted to elope and Jeff wanted a wedding, so they found a happy medium by planning a destination celebration with an intimate guest list. They invited 60 guests to join them on the Italian coast—at a favorite spot they're visited years prior—on September 16, 2017, and turned to planner Marcy Blum to create their classic, Italian celebration with an Old Hollywood vibe. “Marcy was my wedding fairy godmother,” says Annie. “She understands sophistication, elegance, and a damn good party, and she immediately understood what I wanted our wedding to be.” The couple’s guests were dressed in black tie, and the venue was dressed in an abundance of local flowers and glowing candlelight. Photographed by Gianni di Natale, this spectacular celebration will take your breath away. Keep reading for more!

Photo by Gianni di Natale

They’d had a magical trip to Villa Tre Ville in Positano, Italy in 2015, and had no question that it would be the perfect place to share with their closest family and friends. “Jeff is in the hospitality industry, and we’re always thrilled to find unique places with unforgettable experiences,” says Annie. “Villa Tre Ville has so much character, personality, and charm.”

Photo by Gianni di Natale

As a hint of what was to come, the couple’s invitation suite, created by Stephanie Fishwick and printed by Alpine Creative, featured crawling floral vines and the region’s iconic citrus fruits.

Photo by Gianni di Natale
Photo by Gianni di Natale

“I knew I wanted a form-fitting, sweetheart dress with lots of lace,” says Annie. “I showed my Pinterest board to my consultant, Shay, at Kleinfeld, and he immediately came back with the most beautiful options.” In fact, the bride couldn’t decide between the first and second gowns she tried on so she got both! The gown she selected for the ceremony featured a sheer deep-v neckline, a corset bodice, and a dramatic lace-edged train.

Photo by Gianni di Natale

To match the sexy, feminine style of Annie’s wedding gown, her ‘maids wore custom black silk charmeuse gowns with plunging necklines. “I was inspired by an ombré pink Zac Posen gown I’d seen," she says. "We had it recreated in black to fit each girl’s measurements perfectly.”

Photo by Gianni di Natale

The ceremony took place overlooking the Tyrrhenian Sea, where an aisle of white rose petals led to a white floral chuppah.

Photo by Gianni di Natale

Monogrammed cones held petals for guests to toss after Annie and Jeff’s first kiss.

Photo by Gianni di Natale

Jeff wore a Tom Ford tuxedo with a white jacket, while his groomsmen wore black. “We didn’t have a first look,” Annie remembers. “When I turned the corner to walk down the aisle and we locked eyes, we both started to cry. It was deeply emotional, and I’ll cherish that feeling forever.”

Photo by Gianni di Natale

The groom’s father walked the bride down the aisle. "Irwin has so lovingly filled the void of my father," she says. "He has four sons, so it was special for him to have that experience, too.” Annie and Jeff wrote their own tear-jerking vows, which included promises Annie made to Jeff’s two children.

Photo by Gianni di Natale

“Jeff’s vows were so sweet that I went in for a kiss as soon as he was done—well, before it was time,” Annie says, laughing. “It just felt so natural, I couldn’t help it.”

Photo by Gianni di Natale
Photo by Gianni di Natale

Marcy Blum created an enchanted transition from the ceremony to the reception, as the couple and their guests made their way down a path dripping in purple blooms.

Photo by Gianni di Natale
Photo by Gianni di Natale

A canopy of lilac and lavender-colored flowers hung above the tables, which were lit with gold candelabras and covered with pink and purple flowers in gold vases. Each place setting featured a monogrammed plate, custom menu, and gold-rimmed glassware.

Photo by Gianni di Natale

Jeff and Annie shared their first dance, overlooking the ocean, to “Maybe I’m Amazed” by Paul McCartney. “We’ve been to a few of his concerts together, and that song has become really special to us,” Annie says. After a few classic spins, the couple decided to break out their own moves.

Photo by Gianni di Natale
Photo by Gianni di Natale

The couple loves simple, approachable, and beautifully prepared food, so their menu embraced Positano’s fresh and local cuisine. Grilled shrimp scampi was followed by house-made ravioli filled with ricotta. Main courses were served tableside, where lights (tucked inside the canopy of blooms) gave the al fresco reception a warm and inviting glow.

Photo by Gianni di Natale

A wall of white and blush roses created a stunning backdrop behind a pink velvet couch, which was perfect for late-night photos!

Photo by Gianni di Natale

An overhead installation of white flowers and strands of crystals surrounded an intricate chandelier—a decidedly Italian take on a disco ball.

Photo by Gianni di Natale

“While there were lots of moving parts, Marcy’s organization and understanding of my aesthetic made it very easy to pull the trigger and go,”Annie explains. “Remember, your wedding is meant to be a celebration of love. Don’t argue about the plans, and try to enjoy it. This will be the best time of your life!”

Wedding Planner: Marcy Blum Associates || Venue: Villa Tre Ville || Bride's Dresses: Pnina Tornai || Bride's Veil: Pnina Tornai || Bride's Clutch: Edie Parker|| Bride's Shoes: Aquazzura || Makeup: Lawless Beauty || Bridesmaids' Dresses: Belle New York || Groom's Attire: Tom Ford || Groomsmen's Attire: Tom Ford || Floral Design: Malafronte || Paper Products: Alpine Creative, Stephanie Fishwick || Catering: Villa Tre Ville || Cake: Monily Bakery || Entertainment: Elan Artists || Rentals: Nuage Designs, La Tavola Fine Linen, Cannata & Partners, Wedding Solution in Italy, PosaFlora || Photography & Videography: Gianni di Natale

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