Heather Dockweiler's wondrous world of hats in Naples

In honor of Naples Botanical Garden's annual Hats in the Garden fundraiser, Heather Dockweiler—who often takes home the award for best dressed—shares her whimsical toppers of the last decade.

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Heather Dockweiler has been involved with Naples Botanical Garden’s top fundraiser, Hats in the Garden, even before there was a formal garden. She joined the event committee with her mother, Simone Lutgert, in 2005. Two years later, Heather juggled planning her wedding with chairing the event. “Our venue was a construction site with a lot of dirt,” she recalls.

Hats has certainly grown since, becoming one of the largest and most fruitful events of the season, with millions raised for the Garden’s mission of environmental education and preservation. The event is also Heather’s favorite of the season, and she’s developed traditions to amplify the day. Since 2007, she and a group of friends have descended on Third Street South, stopping traffic to take a photo in the middle of the street, then hopping between Campiello and Sea Salt for snacks and cocktails in full Hats garb. “[It’s] a bit of a spectacle, but I saw it as a marketing opportunity for the Garden,” she says.

In 2013, for the event’s 10th anniversary, a friend encouraged her to take a chance with a bold design. Heather has continued to go all out since, prompting eventgoers to wonder what she’ll wear next. While Heather keeps plans for future styles closely guarded, she shares an intimate look into her decade of fabulous toppers here. Each has a personal inspiration—a cherished memory, a playful nudge from her daughter, a dress she adores—but all point back to the cause. “The Garden is truly a gift to our community,” she says.

Black Swan [Pictured Above]

In 2013, Viv Romeo, who was a stylist at Marissa Collections, encouraged Heather to do it up for Hats’ 10th anniversary. “In celebration of the transformation of the Garden and how much it had grown, I was ready to find a hat that was also transformational,” Heather says. When she first saw the Arturo Rios-designed piece at Marissa, she was floored. Arturo created the hat, inspired by Lady Gaga, with black goose feathers and 15-inch-tall wings (the fashion icon later wore the design in her “G.U.Y.” music video). The piece inspired Heather to step into the spotlight in honor of the Garden. “I’m more of a behind-the-scenes person,” she explains. After her 2013 look, she was hooked on theatrical toppers.

Teacup

There’s one special hat you surely recall but won’t see reflected in these pages: the Top Hat fashioned from hair by Louis Boutier of Naples-based 50Fifty Creative Services. Heather wore the ephemeral style in 2017.

The piece was partly inspired by this mossy Teacup topper depicted that Heather had worn to Viv’s bridal shower. Her daughter, Celie, remembered the fascinator, and when the two were watching artistic hair stylists’ videos on YouTube, Celie had an idea. “She turned to me and said, ‘You know what would be cool, mommy? If you made a hat out of your hair!’ This got my wheels turning,” Heather says.

For the 2017 topper, Louis wove most of the Top Hat using hair extensions, then pinned the look onto Heather’s head, weaving in her own hair to make the whole piece appear as one.

(Photo by Kelly Jones)

Cherry

Despite the originality of her Hats style, Heather isn’t one to plan too far in advance (the 2022 outfit came together the day before the event). This Pearls & Swine fascinator was intended for the 2015 Confection Collection-themed Hats in the Garden. The piece would be the ‘cherry on top’ of a REDValentino cherry-printed dress she found at Saks Fifth Avenue, but the frock was only available for pre-order. Still, Heather was enamored by the look and ordered it for the 2016 festivities. “This is probably the only year that I have been that prepared,” she says with a laugh.

(Photo by Kelly Jones)

Cherry Blossom

Her hubby, Jamie, has been by Heather’s side at the event since she chaired it in 2007, making her 2014 Cherry Blossom fascinator extra special. “The sights and sounds of the Garden trigger detailed memories for me,” she says. The event’s theme that year, Couture et Fleurs, reminded Heather of a trip she and Jamie took to see the Japanese cherry blossom trees that only bloom a few weeks out of the year. When the Garden challenged designers to create looks from 80 percent organic, botanical material, Heather knew she wanted to channel the famed pink flowers with an Arturo Rios handmade design. “It was love at first sight,” she says.

(Photo by Kelly Jones)

Burgundy Feather Bomb

“I love the pageantry and the pomp and circumstance of wearing a hat or a fascinator,” Heather says. This coque feathers

fascinator from Hats by Cressida delivers on the drama. Heather was ready to go with her Burgundy Feather Bomb when the Garden’s event was canceled in 2021 due to the pandemic. Not one to let a good design go unworn, Heather donned the headpiece at the Community School of Naples’ World Class Polo fundraiser in December. “The movement of the feathers—how they blew in the wind and reflected the sunlight—made it so whimsical,” she says.

(Photo by Kelly Jones)

Swinging Lady Scene

In 2018, Heather commissioned local artist Silvina Marzari, who trained at New York’s Fashion Institute of Technology, to create a piece inspired by the outfit Heather selected for the event—a Weekend Max Mara toile-printed look from the brand’s Royal Ascot-inspired Trophy Day collection. The women met when Silvina designed costumes for Celie’s productions at Naples Performing Arts Center. Silvina spent more than 30 hours hand-sculpting the miniature figures with cold porcelain, sewing their clothes, and constructing the base from Styrofoam and wire. “This was an invitation to create with no boundaries,” the artist says.

Flytrap

Heather’s 2022 fascinator—made of Dupioni silk and handpainted by Tel Aviv-based Maor Zabar Hats—has been among her most buzzworthy. It’s also her most personal.

The piece shows a Venus flytrap attempting to catch a butterfly. “I have had a deep affinity for butterflies as far back as I can remember. Over the past 20 years, they have become even more significant,” she says, adding that her family hosts butterfly releases at funerals and weddings to celebrate loved ones lost. “When I see one flutter by, I take it as a sign from a loved one and spend a moment reflecting on their life and my connection to them.”

Having recently lost her stepbrother, Kurt Lutgert, to cancer, Heather wanted to keep him close to her heart: “The Venus flytrap represents persistence; the butterfly represents change, comfort, hope and positivity.”