Kaitlyn Bennett

In a digital world, Kaitlyn Bennett decided to practice a handcrafted art form: She started The Lettering Bar, specializing in calligraphy and engraving.

Bennett creates everything by hand from her Naples home—wedding invitations, event menus, even custom glassware. “Calligraphy adds a nice personal touch,” she says.

She has long had an artistic side, taking creative classes in high school and college. Like many people, she found that she had time on her hands during the pandemic; she saw some online videos of calligraphy and decided to give it a try. The trickiest part, according to Bennett, was getting used to the specialized pens and writing instruments. “It’s something anyone can do,” she says. “It just takes a lot of practice.”

Calligraphers are few and far between in Southwest Florida, so once she got the word out, business started rolling in. She’s found her work is in demand for weddings and other events where people are looking for something unique, such as mirrored welcome signs or engraved wine glasses. She got the business off the ground primarily by networking with local wedding and event planners, and also has an extensive social media presence that draws in clients. But so far, she’s found even more success from happy clients and planners who pass along her information. “There’s a great niche for this type of art in this community,” she says.

Bennett is looking to grow The Lettering Bar’s business modestly in the area, and she does travel frequently to host calligraphy classes around the state. She encourages people to look at calligraphy not so much as a practical tool but as art—something that can be shaped by the practitioner’s own creativity. “I just want to share this art form with as many people as possible,” she says.