Leilani Bennett is curled up in the corner of the sofa on her balcony overlooking the course at Tiburón Golf Club. She’s dressed for comfort in a black Michael Kors T-shirt, Lululemon leggings, and iRi sneakers—with a bit of a heel, because her glamour always shines. The founder of Bennett Interiors and the recently opened retail luxury furnishings boutique Home Philosophie on Fifth Avenue North sees inspiration in everything.
“The balcony is a sanctuary where I spend a lot of my time creating, writing [including a screenplay and five novels], and imagining what’s next,” says Leilani, who has lived in Naples for nearly 36 years and seen it grow from “a sleepy little fishing village” to what it is today. A free spirit, Leilani moved to Naples on a whim after a childhood crush she hadn’t seen in some time suggested it. Six months later, they married.
She believes that, as a Libra, she has a deep need for balance, an asset in her line of work. “I see things that are out of place when others don’t,” the 25-plus-year veteran interior
designer explains. “I’ll analyze a room and realize I need to move an object one inch to the left to make the room feel right. But in terms of creating a composition, balancing every object is too contrived for my taste. Arranging accessories in an asymmetrical fashion is far more beautiful, as nature intended it to be.”
Her parents largely influenced her career choice. Her father, Darryl, owned a carpet store. “We had carpet everywhere in our home, even in our bathrooms, which was considered special back then. It would definitely be a faux pas now,” Leilani says with a laugh.
Her mother, Shirley, changed the house’s furnishings seasonally. “It was quite a production,” says Leilani. “Everything from the windows to the walls—sofa, tables, beds, and artwork—had to be changed. I would help her space plan and my brothers would move the furniture to where we directed them.” That was a kind of training ground for the future designer, where she learned the importance of planning and project management. Leilani’s mother also taught her to choose quality over quantity, a rule she still follows. “I encourage my clients to purchase fewer items but spend more per item, which, in turn, will make a beautiful statement.”
She was raised along with five siblings in a bucolic setting on a 45-acre farm in Waite Hill Village, Ohio, surrounded by rolling hills, pastures, and ponds. “We climbed trees like monkeys, ate fresh fruit straight from the orchard, played in the corn fields until sundown, and swam in the Chagrin River,” says Leilani. “Picking weeds, bailing hay, and waking up at dawn to feed the cows never felt like chores.”
Some 4,000 miles away in England’s countryside near Stonehenge, Leilani’s daughter, actress Haley Bennett, has just come in from her own pastoral environs—tilling her garden, checking on her vegetables, and cutting flowers for a sweet-smelling bouquet. She has dirt under her nails and a smile on her face.
While Leilani’s name means “heavenly flower” in Hawaiian, Haley is the Bennett who grows roses, dahlias, daisies, and lavender along with a seasonal rotation of vegetables and herbs. Recent additions of lemongrass, ginger, and chili peppers help satisfy her Thai food craving. The culinary arts represent one more way Haley expresses herself. “Time is never wasted if I am in the garden planting or harvesting, or in the kitchen preparing food for my friends and family,” she says.
Like her mother, Haley is a blonde beauty with a bohemian lifestyle and a deep well of talent bubbling over with creativity. She positively luminesces on-screen, whether she’s starring opposite Chris Pratt and Denzel Washington in The Magnificent Seven, alongside Emily Blunt in The Girl on the Train, or going toe-to-toe with Amy Adams and Glenn Close in Hillbilly Elegy.
Leilani says when she named her daughter after Halley’s Comet, she believed Haley would one day be a star. “At the time, I certainly didn’t know how, why, or when it would happen,” Leilani says. “I just spoke of it with a strong conviction, then let it go into the universe.
Haley’s affinity for acting and singing began early. As her mother recalls, Haley, just shy of 2, was sick and wouldn’t stop crying. So Leilani put on The Wizard of Oz in hopes of soothing the screaming toddler. “She could barely talk, so I couldn’t believe how crystal clear and pronounced her little singing voice was, and how she could hit the high notes on ‘Somewhere Over the Rainbow,’” says Leilani. Later, Haley acted in school plays and dreamed of one day becoming like her idols Judy Garland, Barbra Streisand, and Julie Andrews.
Although “her father [Ronald Keeling] and I didn’t do anything special to groom Haley for stardom,” Leilani says, she did put her own work on the back burner and move to Los Angeles for four years to help get her daughter’s career off the ground. In just three-and-a-half months, the 17-year-old landed a role in the 2007 film Music and Lyrics with Drew Barrymore and Hugh Grant.
Mother and daughter continue to flourish in their lives and careers. Perusing Leilani’s home designs on her website and gorgeous interiors on Instagram reveals the tranquility that runs through her work, whether the design is modern, contemporary, or traditional, or whether the project is a 3,000-square-foot condo in downtown Naples, a remodel in Olde Cypress, or converting a dining room in Royal Harbor into an enclosed wine cellar. “A well-executed design will always feel tranquil,” she says. “Kind of like a breeze, it just feels good but you don’t know why.”
As for Haley, she plays Roxanne to Peter Dinklage’s Cyrano in a modern movie adaptation of the off-Broadway play Cyrano, written by Dinklage’s wife, Erica Schmidt. The movie, scheduled for release in December, was directed by Haley’s partner, Joe Wright, who has helmed cinematic classics like Pride & Prejudice and Anna Karenina. “[Cyrano] was filmed in Noto, Sicily, during the pandemic,” Haley says. “We lived in a seventeenth-century villa called Seven Rooms with some of the key cast and crew members in a safe bubble. The sets were very luscious and transportive.”
Now a mom herself to 2-year-old daughter Virginia, Haley remembers fondly what it was like growing up in a creative household. Her older sister, Adella, now a human resources supervisor, has a side business making elaborately decorated cakes, and younger brother Quinton is an avid reader, writer, and the family philosopher. “My earliest memories are of paintings my mom did, mostly large-scale flowers or couples in an embrace, dancing across canvases,” says Haley, who has her own masterful eye for photography.
Says Leilani, “I’m so blessed in a thousand ways to have three awesome, talented children and beautiful grandchildren, who are all very loving and protective of me. I’m proud of them all. Not to mention, I feel as if I’m the luckiest woman in the world to be loved to the moon and back by my husband, Tim Holobinko.”
Due to the pandemic, Haley hasn’t been able to visit her mom in Naples recently, but they have shared a lot of FaceTime calls. Haley misses “the salty-sweet Gulf Coast air, the people with their golden tans, and the laid-back way of life.” Some of her favorite memories include the “impossibly quaint” stores on Fifth Avenue South, coconut shrimp and live music at Tommy Bahama Restaurant & Bar, and shopping at Waterside Shops. When she visits, she usually requests Leilani make her “famous” red beans and rice, and they might stop into one of Leilani’s favorite restaurants: Bistro 821, Campiello Ristorante & Bar, Mr. Big Fish, or the Lake Park Diner.
Artistic in so many ways, Leilani strived to instill a sense of wonder and creativity in her kids, often leading by example. Singing is the one exception. “All my children have phenomenal singing voices, but I can’t sing at all,” says Leilani. “When they were young, I would try to sing to them and the little boogers would nicely say, ‘Mommy, can you just read to us?’ But I can dance and I taught them all how to bust a few moves.”
The ability to let criticism roll off her back helped propel Leilani to success. “Since I was young, long before the famous book The Secret, I have always brushed off negative actions of others and smiled despite adversity,” she says. “I wouldn’t have started a business, taken a sabbatical to Los Angeles, and then reopened my design business if I had listened
“Raw instinct has always led me to do what’s best for my family and myself. If you let others guide you based on their negativity, the results will be what I call ‘mistaken intuition,’ and that’s when doors close,” Leilani adds. “It’s not always easy, but you have to believe in the impossible to make things possible.”