Legacy & Style: A Conversation with Kevin Tillis of Kennedy Gray

Hi, my name is Kevin Tillis. I’m the founder of Kennedy Gray, a menswear brand based in Charleston, South Carolina focused on classics with a little character. The name “Kennedy Gray” is deeply personal. Kennedy is my middle name, and Gray is my mom’s maiden name. But more than that, it’s a tribute to my family’s heritage on Lake Rabun, where we’ve had Graymont Cottage since 1927.

That place - rugged, vintage, and full of nautical prep deep in the evergreen Appalachian Mountains. Wooden boats, old architecture, and the timeless style of my great-grandfathers around the lake are the foundation of Kennedy Gray’s aesthetic.

 

A Legacy Woven Into Fabric
Being in that same space where my family has lived and loved for a century has inspired what I’m building. Kennedy Gray is more than clothing, it’s a continuation of a story. The style is vintage nautical prep, but the heart is legacy. I want people to wear Kennedy Gray and feel like they’re part of something lasting.

Purpose in Every Thread
What they wore back then wasn’t just stylish—it was intentional. That’s what I’m trying to recreate. For me, creating tangible products is a way to connect with people and live out a calling. It’s about more than fashion—it’s about meaning.

I want people to think about what they wear, not just consume it. I want them to understand the story behind it. That’s why I design with longevity in mind. I want Kennedy Gray pieces to be worn forever, loved forever, and made to last.

Sustainability as Stewardship
Sustainability, to me, means longevity. It’s how I live, how I build, and how I produce. That includes everything down to the packaging. The places that inspire me—Lake Rabun, the Charleston coast—are alive because of nature. I surf and swim in the ocean almost every day. Taking care of that is part of stewarding the planet well.

That’s why I made the shift to sustainable packaging. I realized I could make the most sustainable shirt, but if I sent it in packaging that didn’t align, I wasn’t doing justice to the brand, the customer, or the planet.

New Earth Approved
I discovered New Earth Approved packaging through surfing. It was a lightbulb moment -realizing I could produce packaging that aligned with my values. Over time, I found materials that truly suit the Kennedy Gray brand.

Running this business has always been about planting seeds and stewarding resources well. That’s been the journey.

Timeless by Design
“Vintage” gets thrown around a lot, but to me, it means quality. I use natural fiber fabrics—organic cottons, linens, and wools. I stay away from synthetic “performance” materials that don’t align with the brand’s ethos.

The aesthetic is timeless. I look back at my great-grandfather’s polos and shirts—made ethically, worn with care. People used to think about what they wore. That’s what I want to bring back.

What’s Next
I see what I create as part of me. I’m responsible for it and its lifecycle. Over the years, I’ve refined what Kennedy Gray stands for. Now, there’s a strong foundation—and I’m ready to grow it into whatever’s next.

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