Jamie Dockweiler | The Family Man
As one of the lone men in the crowd at Hats in the Garden—the Naples Botanical Garden’s November event that acts as the unofficial kickoff to season—Jamie Dockweiler is used to standing out. Dockweiler, who dons a hat from his forays to the Kentucky Derby, began attending in 2007 when his wife, Heather, chaired the elegant fundraiser. Hats isn’t the only fashionable affair for the Dockweilers, who have co-chaired the Community School of Naples’ Angel Ball. They regularly attend the American Heart Association’s Heart Walk, and he serves on the board of the Naples Zoo.
Dockweiler, a sales associate at Premier Sotheby’s International Realty, appreciates the flexibility of real estate because it allows him to focus on his daughter, Celie Rose, 8, and son, Maxwell, 10. Being present for his children and developing enduring bonds, just as his own mother did, has been his plan all along. “If anyone asked me what I wanted to be when I grew up, it was to be a dad,” he recalls. “Time with family to me is the most important thing.”
Although he’s gained a reputation as a stylish man, he admits that fashion hasn’t always been on his radar. “I was so involved in sports, I didn’t pay too much attention.” It was while pursuing a degree in sports management at Kennesaw State University that he worked part-time at the Gap and became more aware of what he wore. “You get great discounts, and that’s when I started building a closet,” says Dockweiler, who now prefers designers such as Brunello Cucinelli and John Varvatos.
While Dockweiler thrived on sports, he knows they’re not for everyone and stresses the importance of kids finding a place where they belong. For Celie Rose, that place has been the Naples Performing Arts Center, where she’s taken the stage in 10 performances. From his parental perch, Dockweiler has begun helping the nonprofit, which started with a few dozen students and now has more than 700, including those with special needs, enrolled in dance, drama, and music classes. “There is a lack of performing arts in schools today,” he says. The center “encourages their love for the arts, builds their confidence, and helps them grow.”
Ron Ciesla | The Consummate Gentleman
When he’s not dressed for the fairways, Ron Ciesla is ready for the boardroom. No matter where he’s headed, Ciesla is a firm believer that looking good is a gentlemanly sign of respect.
“When you dress nicely, people treat you differently,” he says, adding that it even applies to travel, a tip he’s shared with his grown children. “Always wear a blazer and you’ll be treated differently by airline staff. I always try to look like a gentleman. I think it’s very important, and we’re losing that. The whole thought of civility and being a gentleman is getting lost. There’s a sloppiness that has crept in. You can be casual and not be sloppy.”
Ciesla adopted this appreciation for formality at a young age. Growing up in Bernardsville, New Jersey, he explains that his family was relatively poor, but he took note of how one of his uncles made an effort “to always have a style about himself,” he recalls. “It was something I admired about him. At family gatherings, he might have a nice fedora or a blazer and a tie, little things that set him apart from everyone else.”
A childhood in New Jersey gave way to a career in New York City. In 2001, he was recruited for a position at Northern Trust’s Naples office, where he’s senior vice president and managing director. The timing felt right to relocate his family to the small coastal town he first visited in the late 1980s. “After 9/11, New York changed for me,” he says.
Ciesla didn’t link up with golf until he married his wife of 32 years, Karin, and they started playing together and meeting new friends. Both of their children gravitated toward the sport, even participating on school teams. “Golf is my passion,” says Ciesla, who serves on the LPGA Foundation board and has a desire to bolster women’s professional and social networking opportunities through the game. “It’s very useful for the work that I do. I saw the benefit it brought my son as he pursued it. I saw doors open. I saw it to a different extent for my daughter. There’s a civility to it that’s not present in other professional sports.”
Dominic Lacquaniti | The Couture Craftsman
“Jackets are not negotiable,” pronounces Dominic Lacquaniti, a man of bespoke style whose passion for fabric is in his blood. “Guys have to dress up. It changes your outlook on life. I’m changing Naples one sport coat at a time.”
The force behind the custom clothing atelier D. Lacquaniti Bespoke grew up napping atop fabric piles at his father’s New Jersey tailoring business. He studied briefly at the Fashion Institute of Technology before learning alongside textile designers in New York City for 17 years. In 2012, he joined his father, Rocco Lacquaniti, who’d relocated Rocco’s Tailor Shop to Naples in the late 1990s.
Since taking over operations six years ago, Lacquaniti has envisioned a “Naples look” and promoted the lady’s tuxedo. Three local tailors create D. Lacquaniti Bespoke’s handmade men’s and women’s clothing, along with New York–based “old-school Italian tailors I’ve known forever” he says.
When it comes to inspirational fashion designers, Lacquaniti first looks to fellow Italian Gianni Versace. “He’s from the same part of Italy as my family,” he explains. “He had to fight really big people to become successful. He was the underdog.”
Demand for Lacquaniti’s bespoke creations is so high that his concierge alteration services come second—and only by appointment. These days, “I’m getting pulled to Miami” for high-styling clients including celebrities and athletes, says Lacquaniti, who’s considering other ways to expand. “It’s not work; it’s my passion. I love seeing change in people. It’s my medicine. I love that my clients give me the opportunity to create beautiful things for them.”
For his own clothing choices, Lacquaniti—who possesses a quick wit and disposition as sunny as Naples—confesses that he often dresses based on his mood. “If I’m feeling down and want fun, I will wear a brighter color. We can do that. It’s Florida.”
Ken Kelly | The Jet-Setter
Naples native Ken Kelly keeps his suitcase stocked with Untuckit casualwear—a logical choice for the successful business leader and humanitarian who spent a third of the last calendar year traveling.
As a wing commander for Angel Flight in Southwest Florida and a top-rated roofing expert, Kelly has gone on many hurricane-relief trips. He’s visited 60 countries and flown nonprofit missions for 16 years, racking up 1,000 piloting hours in his 2007 Cirrus SR22 after Hurricane Dorian ravished the Bahamas. He met his fiancée, Jennifer Jebrock, a clinical pharmacist at Jackson Memorial Hospital, after transporting a teenaged liver transplant patient from Naples to Miami.
The president of Kelly Roofing, which was named Roofing Contractor of the Year in 2019 by an industry magazine, was hand-selected to consult on flashing and waterproofing for Tesla’s Solarglass Roof. He’s recently made several trips to Northern California, in fact, for research, development, and training for the new photovoltaic systems.
After graduating from Barron Collier High School in 1993, Kelly took over operations of the business that his father, Joe Sr., established in 1972. He notes that Kelly Roofing is guided by the Japanese philosophy of kaizen—making a lifetime commitment to learning and improvement. “Being selected to work with Tesla really matches that core value,” he says. “It allows us to be cutting edge and continuously improve, not only internally but for the entire industry.”
And while Kelly is constantly progressing in business, he does take a slightly more restrained approach to fashion. “I consider myself edgy conservative,” he says. “You think I’m conservative until you see my socks. I have some pretty funny, crazy socks. That’s where personality comes out.”
Kelly has plenty of opportunities to share this fun side. He’s chairman of the Collier County Code Enforcement Board and served on the county’s Affordable Housing Advisory Committee for a decade. Years ago, he helped establish Hope Contained, a nonprofit that provides housing by refurbishing steel shipping containers. Kelly, who was a single dad to his son, Austin, gives back to the community simply because “I truly believe in the pay-it-forward mentality,” he says. When he needed it most, “there were a lot of people who went out of their way to help me.”
Ralph Stayer | The Haute Husband
Ralph Stayer is a philanthropic leader in Naples, where he and his wife, Shelly, have had a tremendous impact since moving to Gordon Drive just a decade ago. Next month, he’ll be at her side during the grand opening of the Shelly Stayer Shelter for Human Trafficking and Domestic Violence. Built by the Shelter for Abused Women & Children in Immokalee, the facility is the first of its kind in the nation.
“This is Shelly’s thing, and I totally support her,” says Stayer, adding that they focus 95 percent of their philanthropic efforts on women and children. “We’re happy to do anything we can to help, especially to make people aware of human trafficking.”
Stayer credits his wife, a fellow Wisconsin native, for helping to make him a man of style. “As long as she keeps dressing me, I’ll continue to be fashionable,” he says, laughing. “My wife always looks fabulous so I really don’t have a choice but to dress well. Otherwise, we’d be an odd-looking couple.”
Stayer has been recognized nationally as a top CEO for transforming Johnsonville Sausage from a butcher shop his parents started in Johnsonville, Wisconsin, in 1945 to a global brand sold in nearly 50 countries. These days, he’s slowly stepping away from his duties and coaching the next generation to take over. “It’s always been my intention to create a family legacy,” he says, noting that all seven of his children are involved in the business. “God used me to build this business, and I’m excited to have my children as stewards.” He remains chairman of Johnsonville Holdings, with three subsidiaries and multiple investments.
This year is proving to be a packed one for the Stayers. The couple will witness the weddings of two children before embarking on an exotic trip to Kazakhstan, Bhutan, Lebanon, and India. But whether he’s working or relaxing, the sausage king remains an avid reader who devours more than 150 books a year.
He also co-authored the 1994 best-seller Flight of the Buffalo: Soaring to Excellence, Learning to Let Employees Lead. It was fueled by his popular 1990 Harvard Business Review article, “How I Learned to Let My Workers Lead,” which is still required reading for most business students. Says Stayer: “I think it’s a timeless message.”
Shot on location at Campiello, Naples
Grooming by M Room, Naples