Holly Henry on the Cowboy Bootmaking Community's Sustaining Power (Also: Saddles)

I will tell anyone who dares listen that handmade bootmaking—and perhaps specifically, cowboy bootmaking—is the highest form of leatherwork as functional art. And then I started paying attention a bit more to saddlemaking and was like damn ok maybe they’re tied.

Parker, Colorado-based custom bootmaker Holly Henry knows a ton about both. Holly grew up riding horses outside Houston, Texas, and was, quite remarkably, a professional photographer by her early teens. While studying photography in college, she took a shoemaking course—which changed everything.

After some skill-informing detours through millinery (that’s hat-making!), tailoring, and, yes, intensive saddle repair, Holly began training to make cowboy boots, moved to Colorado, and struck out on her own as an independent bootmaker. Which is exactly where we pick her up, on the Shoecast.

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We'd better see you at Stitchdown Chicago 2026—the world's fair of shoes and boots and leather and more—Nov 6-7 at Artifact Events.

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