From classic captain’s hats and deck shoes to technical apparel built for long days at sea, a captain’s wardrobe has always been about more than appearance — it’s a reflection of life on the water.
Long before someone takes the helm, there’s often one piece of apparel that quietly signals a connection to the water: the captain’s hat.
For generations, the captain’s hat has symbolized confidence, experience and a deep respect for maritime tradition. Whether worn by commercial captains, yacht owners or recreational boaters, it remains one of boating’s most recognizable symbols and an enduring piece of nautical heritage.
Historically, captain’s hats have been produced in both black and white, with darker wool hats often favored for year-round wear and white versions traditionally associated with summer uniforms. At Benford Yacht Hat, however, founders Jeanie Benford-Jordan and Ray Jordan focus exclusively on the classic black captain’s hat, believing it offers timeless style while remaining practical for everyday use on the water.
Few companies are working to preserve that legacy quite like Benford Yacht Hat, a family-owned business based in Inverness, Florida. Since 2017, Jeanie and Ray have produced American-made captain’s hats inspired by the classic yacht caps once manufactured by the Lancaster Hat Company. Their mission is not simply to make hats, but to ensure an iconic piece of American boating history continues to be worn by future generations.
A captain’s look, however, extends well beyond a single hat.
Today’s boaters have access to high-performance apparel designed to make long days on the water safer and more comfortable. Lightweight technical shirts provide protection from the sun, waterproof outerwear shields against spray, non-marking deck shoes offer secure footing on wet decks and polarized sunglasses help reveal fish beneath the surface. While boating apparel continues to evolve through advances in technology, many of its most recognizable pieces remain rooted in tradition, making boating one of the few lifestyles where modern performance and maritime heritage naturally coexist.
A captain’s wardrobe often reflects a lifetime spent on the water. Every well-worn pair of deck shoes, weathered foul-weather jacket or faded cap can tell the story of early mornings leaving the harbor, afternoons spent chasing fish offshore, family cruises to Catalina Island and evenings watching the sunset from the flybridge.
Perhaps no single piece of apparel carries that history more than the traditional captain’s hat.
For Jeanie Benford-Jordan, that tradition stretches back generations.
Growing up in Rochester, New York, she was introduced to boating almost from birth as her parents, Jim and Margaret, spent decades sailing Lake Ontario before eventually fulfilling a lifelong dream of cruising the Intracoastal Waterway and the waters of Florida and the Bahamas. Boating became more than a pastime for the family. It became part of their identity.
That passion for life on the water extended throughout the Benford family. Her brother, renowned yacht designer Jay R. Benford, has spent more than six decades designing custom cruising sailboats, tugboats, liveaboards and expedition-style yachts, while her uncle, Harry Benford, earned international recognition as both a naval architect and marine engineer.
That lifelong connection to boating eventually inspired Jeanie and Ray to preserve one of the sport’s most recognizable traditions.
For decades, Ray wore captain’s hats produced by the Lancaster Hat Company, a respected American manufacturer whose yacht caps became a familiar sight among captains and boating enthusiasts throughout the country. His appreciation for the hats began long before Benford Yacht Hat was established.
“My husband, Ray Jordan, a Navy Seabee, has worn this style of hat for over 50 years,” Jeanie said. “He discovered his first one, a used Lancaster hat, at a flea market when he was in his twenties. Over the years he owned several of them.”
When Lancaster closed its doors in 2011, the couple realized that an important piece of American nautical craftsmanship could disappear along with it.
“We were very disappointed when Lancaster closed their doors in 2011,” she said. “We decided to fill that gap and keep the tradition of American-made captain’s hats alive, opening Benford Yacht Hat in 2017.”
According to Jeanie, the classic captain’s hat has become synonymous with her husband.
“The captain’s hat has become his trademark. He wears it with pride everywhere and loves how it commands respect and creates conversations wherever he goes.”
Today, the Jordans continue producing Benford Yacht Hats from their Florida workshop, combining traditional craftsmanship with durable materials intended for years of use on the water.
Jeanie said the difference between a Benford Yacht Hat and many novelty versions begins with the quality of its construction.
“A Benford Yacht Hat is recognized by its classic style, premium materials, fully lined construction and nine distinct sizes for a perfect fit.”
She explained that every hat features genuine gold bullion embroidery rather than the flat embroidered patches commonly found on inexpensive costume versions.
“Our hats use genuine gold bullion embroidery in detailed three-dimensional craftsmanship that creates a rich, more refined appearance than flat stitching in a sewn-on patch. Benford Yacht Hats are designed for real use, combining classic design with American craftsmanship you can see and quality you can feel.”
By comparison, she said many novelty hats are mass-produced using lightweight synthetic materials and one-size-fits-all construction that often loses its shape quickly and lacks the durability expected from a hat intended for years on the water.
Each Benford Yacht Hat is available in nine sizes to provide a tailored fit and is designed to retain its shape season after season. The hats will even float if accidentally dropped overboard.
Jeanie also hopes customers notice the attention given to even the smallest design details.
“One of the details in craftsmanship is the hand-embroidered crossed anchor/life ring insignia.”
She said one longtime member of the Benford Yacht Hat family described the insignia as “a three-dimensional work of art.”
For the Jordans, however, preserving the captain’s hat is about more than craftsmanship alone. It’s also about preserving the memories and traditions that accompany a lifetime spent on the water.
Over the years, customers have shared stories illustrating what the hats have come to represent. During the Wooden Boat Show at Mystic Seaport in Connecticut, Jeanie recalled one gentleman purchasing a Benford Yacht Hat before returning the following day to buy another for his son, describing it as a meaningful father-son bonding experience.
She has also received heartfelt letters from longtime boaters, including Captain Richard C. Sturgill of the steam launch Gizmo, who wrote that he hoped his Benford Yacht Hat would accompany future adventures just as many of his favorite hats had become lasting reminders of cherished memories from years spent on the water.
Although boating technology continues to advance, many traditions remain unchanged. Boaters continue to appreciate equipment that performs reliably while reflecting the pride they take in their time on the water, whether it’s a trusted pair of deck shoes, a dependable foul-weather jacket or a captain’s hat that becomes a familiar companion for decades.
That same philosophy extends throughout a captain’s wardrobe.
Comfortable, functional clothing remains essential for long days underway. Lightweight technical shirts provide protection from the sun, quick-drying shorts stand up to saltwater and spray, non-slip footwear improves footing on wet decks and quality rain gear helps boaters stay comfortable when conditions change. Wide-brim hats and polarized sunglasses have become just as indispensable as navigation electronics and safety equipment.
Even so, tradition continues to play an important role in boating culture. From yacht club burgees flying above the marina to polished brass hardware and neatly coiled dock lines, boating has always celebrated craftsmanship, attention to detail and pride of ownership. A captain’s attire reflects those same values.
Jeanie believes wearing a captain’s hat communicates a respect for those traditions.
“When you wear a Benford Yacht Hat, people know you are serious about boating. You may or may not be a captain, but you are wearing an heirloom-quality nautical hat made in the United States that commands respect.”
She said the hats are designed for boaters who appreciate quality, heritage and timeless craftsmanship.
“This hat is crafted for those who value tradition, quality and timeless nautical style.”
Whether someone is at the helm of a center console chasing tuna offshore, cruising a sailboat to Catalina Island or enjoying a leisurely afternoon harbor cruise, classic nautical style continues to connect today’s boaters with the generations that came before them. While boating apparel has certainly evolved over the years, the enduring appeal of the captain’s hat serves as a reminder that some traditions never lose their place on the water.
