A black and white action shot of Holly Henry sitting on a work bench wearing a cowboy hat while she crafts a handmade boot using a leather making tool.

Holly Henry

Preserving a Legacy

Holly Henry is a bespoke bootmaker based in Boulder, Colorado. For Holly, the art of bootmaking is closely tied to her lifelong passion for riding. Growing up on the outskirts of Houston, Texas, she developed an early appreciation for the craftsmanship and durability of quality boots. Today, when she’s not behind a sewing machine, you’ll likely find her riding trails or summiting mountain peaks with her horses, Kickapoo and Margo.

Holly has traveled the globe to master her craft, learning from skilled boot and shoe makers in Chicago, New York, Eastbourne (UK), Texas, and Colorado. This diverse training has provided her with a well-rounded skill set and years of experience creating custom boots for herself, friends, family, and customers from across the country.

A close up image of an embroidery machine needle producing one of Holly Henry's cowboy boot designs.

The Work

Old Stone Trade collaborated with Holly to create a distinctive cowboy boot that reflects both her expert craftsmanship and OST’s dedication to timeless design.

Every pair of Holly Henry’s handmade boots begins with a custom last—a meticulously crafted mold shaped to the exact measurements of each foot. Once made, this personalized last can be reused for future pairs, guaranteeing a perfect fit every time.

Holly personally handles every step of the boot making process, dedicating an average of 60+ hours of skilled labor to crafting each pair. The welted construction allows for repairs and resoling, ensuring the boots can be worn for decades.