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Beloved ‘Walking Hat Lady’ bids farewell to Sea Cliff


The room was warm, illuminated by a single lamp and appearing almost cavernous. At moments the light caught a jewel or a sequin sewn into one of Anna Jennett’s 200 elaborate, handmade hats, which crowded the shelves and tables.

Looking into one of the mirrored panels of her black boudoir, she adjusted her headpiece, tipping it forward ever so slightly. It was the color of rubies, and had a ribbon adorned with gold music notes tied around it. On its tail hung a bouquet of sparkly, decorative hearts — appropriate for Valentine’s Day.

Jennett, of Glen Cove, has spent the past 50 years creating colorful headwear for nobody but herself, and her creativity has captivated many members of the community. On her daily walk around the neighborhood, the 62-year-old wears one of her many eye-catching hats. She has become known affectionately as “the Walking Hat Lady.”

“When I would want to do my exercises, I would have curlers in my hair, and I sweat so much I wouldn’t want to take the curlers out, so I started putting a hat on,” she said. “And then a holiday would come around and I started dressing the hat up, and before I knew it, it just became a tradition.”

Jennett and her family moved to Locust Valley from Aiken, S.C., in 1960. Her father was asked to work on the estate of the Doubledays, a famed publishing family and the former owners of the New York Mets. “A lot of wealthy people from the Northeast would go down and set up winter colonies [there],” Jennett explained, “and the Doubledays approached my father [because] they needed a caretaker, so we came up here as a family.”

Walking for her life

While her presence is as warm and inviting as the colors she wears, Jennett admits she has always been shy. As a youth she was obese, and over the course of her life she has suffered from a laundry list of health issues, complicated by misdiagnoses. “Almost every year there was a new health problem,” she said, “and through the years I’ve had a hard time with doctors.”

Two months ago, doctors finally determined that Jennett had a rare mitochondrial disease. “They don’t know how to interpret my results,” she said, “or they scream, ‘I don’t even know how you’re alive!’” The doctors had concluded, however, that she was still here for a reason.

When she was 12, she began to “walk for life” to counter her constant ailments. “This walk, and doing my hats, has been my saving grace,” she said. “It’s been like a divine hand helping me cope.”

She walks an average of seven miles a day, seven days a week. She most enjoys walking at Sea Cliff Beach, up the steep hill of Cliff Way, on the stairwell at Tilley Place and along Sea Cliff Avenue. Sometimes she even walks backward.

“To see her walk by was such a lively picture of beauty, color, creativity and energy,” said her neighbor in Glen Cove’s Trousdell Village, Judy DiBartolo. The two got to know each other in the community’s fitness center. “Even there, she had a splash of color,” DiBartolo laughed.

What started as a simple stroll for her health has become a game of “I Spy” for Jennett’s neighbors, who over the years have kept their eyes peeled for a pop of color on their street. During her perambulations she is often greeted with thumbs up and smiles from strangers, and stopped by passersby who offer compliments and well wishes, or longtime friends who just want to chat.

“I always found her so inspiring,” DiBartolo said. “In our world today, to have an unusual, unique person breathing such beauty and such life into our community is a very good thing.”

The rainbow connection

While walking is Jennett’s physical therapy, her hat-making hobby, she said, is a form of rehabilitation. She is a fan of color therapy, an alternative therapy that uses color to heal physical and emotional ailments. She recalls her late husband, Cliff, frequenting yard sales in search of hats she could transform into head-turning works of art. She uses birds, feathers, flowers and butterflies to bring “a bit of sparkle” to her hats.

“It’s kinda like the Charlie Brown Christmas tree,” she said. “If [Cliff] saw a sickly hat that he knew I could fix up, he would come lugging them in. I still have some hats that I haven’t decorated yet.”

Making them, she said, is similar to an addiction. “I can actually feel a craving to create a hat when I get stressed,” Jennett said. “Sometimes at night, I’m dreaming about what hat I’m going to wear or what I want to create [the next day]. That’s what drives me.”

Her creativity has helped her fend off her darkest demons. Having also suffered domestic violence and abuse, she is a survivor in more ways than one. “I took a lot of negativity in my life, and I’m just so glad that I never let that out, and turned it into something positive,” she said. “In spite of my limitations and this dark energy in my life . . . I don’t radiate what hurts me inside.”

Saying goodbye

On Feb. 26, Jennett will return to Aiken to tend to her illness. Earlier this month, DiBartolo organized a going-away party in Jennett’s honor to celebrate the joy she has inspired in the community. And while she had only intended to heal herself on her life journey, Jennett acknowledges, “It’s been bigger than me.”

“Her footsteps are all over the place — we know she was here,” DiBartolo said. “She left behind a message to us all to really care for ourselves, to get out of our own way and to share with others. We’ll miss her, but her impact will be felt forever.”

Jennett described the support from the community as overwhelming. “They have given me so much confidence, love and support, which I never really got,” she said. “My heart and soul is still here, and if I get homesick, Sea Cliff, here I come!”