
Today we’d like to introduce you to Kaitlyn Bennett.
Hi Kaitlyn, we’d love for you to start by introducing yourself.
I’m Kaitlyn, the hands behind all the lettered things! I’m a self-taught modern calligrapher based out of Naples, FL but I’m often traveling throughout the state hosting lettering workshops and live lettering events!
I started my journey creating signs for my own home, and it has now evolved into creating bespoke wedding and event decor, teaching modern calligraphy workshops, custom engraving, live luxury lettering events, and hand-lettered goodies shipped nationwide.
I love love and hearing all of the amazing love stories that come along with the wedding side of this business. I enjoy creating items that the bride and groom can share with their guests and keep for a lifetime!
Can you talk to us a bit about the challenges and lessons you’ve learned along the way? Looking back, would you say it’s been easy or smooth in retrospect?
Definitely not easy! I think any creative and/or entrepreneur can attest to the challenges that come along with starting something from scratch. When I began doing modern calligraphy and engraving, there weren’t many resources for how to get started, pricing, and marketing to clients. Luckily social media has changed that significantly and allowed me to learn from others in my industry, as I’m still the only modern calligrapher in the Naples area and network with people in the wedding industry to offer my services to.
Can you tell our readers more about what you do and what you think sets you apart from others?
I’m a modern calligrapher. I utilize a multitude of tools to create the calligraphy style of hand lettering. This more modern approach opens up the opportunity to customize a variety of items and materials but keeping that signature calligraphy style. I have also expanded into the engraving side of the business. I can now engrave my calligraphy style into glass items like wine, liquor, or perfume bottles. What sets me apart from other sign makers is that all of my pieces are created by hand, and I am always up for customizing a new piece.
Can you talk to us about how you think about risk?
I would consider myself a calculated risk-taker. I like to try new things and be challenged, but I like to do my homework and make sure something is going to be possible before jumping in head first. I have taken risks like reaching out to local business to offer workshops, which they then ran with the idea to incorporate additional types into their businesses. I have taken on more challenging projects like free hand lettering signage on a 6′ piece of live edge wood and in someone’s home as wall and window decor. I’m never 100% sure if the projects will work out, but so far, they have been and it’s amazing to see the end result.
Contact Info:
- Website: www.theletteringbar.com
- Instagram: @theletteringbar
- Facebook: www.facebook.com/theletteringbar

Image Credits
Ali Wanamaker
