Anniversary Edition

Dress boots, Sunday boots, boardroom boots, Special occasion boots...any situation where leather speaks louder than labels, these boots deliver.

I was lucky to get a pair, and they’ve become the one item people comment on more than anything else I own. What I love about them:

1. Build Quality (Legit, Not Marketing-Speak)

Chisos builds these like they expect them to outlive you. Stitching, welt, heel stack, etc...Chisos does not take shortcuts and you feel it when you put them on. In a world where “premium products” often hide cheap internals, these actually feel engineered.

2. Details You Actually Notice

From presentation when you unbox them, to the shaft etching of the Chisos mountains and the hand-cut gator panels: None of it feels gimmicky. An incredible amount of thought and care went into these boots, and you know it the moment you put them on.

3. The Red Line

That single red line in the heel against an all-black boot reminds me of the SR-71 Blackbird: stealthy, purposeful, and cool without needing to advertise it. (As a kid, I thought the SR-71 was as cool as cool could get.)

4. Fit & Comfort (Pay Attention—Gator Is Different)

Alligator does not stretch like cowhide or ostrich. If you’re between sizes, err on the slightly roomier side. For all of my boots, I start with thin socks and transition to thicker ones as they break in. With the gator boots, four years later and I’m still wearing the thinnest boot socks I can find. It's not a problem, these boots feel great, but don’t expect them to “give” like softer leathers.

5. Break-In & Real-World Use

Break-in is minimal. Chisos nailed the insole and the last. Durability? I’ve worn them to dinners, events, and on concrete floors. There has been no peeling or weird creasing. Gator holds up. Travel? Absolutely. They pack flat and don’t scuff easily.

6. Value

These boots are showstoppers and an incredible value for what you get. If they were built by some other legacy boot makers in this hide and build quality, they’d cost triple.

Chisos wild caught Texas gator. A homerun dress boot - I’ve worn these to countless weddings, other formal events, on stage and with jeans as well. Total comfort with an exotic Texas touch that only Chisos delivers. Yep 👊🇺🇸

I’ve had my Chisos Anniversary Edition Gator Boots for a few years now, and I still only pull them out for special occasions—because they’re truly something special. I originally bought them for my wedding in 2021, and they didn’t just complement my tuxedo… they elevated it. I felt like a million bucks walking down the aisle.

The craftsmanship is unreal. The gator is soft, beautiful, and durable, and the design strikes the perfect balance of luxury and classic cowboy boot heritage. They arrived in a custom wooden box with a message engraved inside—one of those small touches that tells you you’re dealing with a company that actually cares. And like all Chisos boots, the insoles make them incredibly comfortable right out of the box.

I’ve owned many boots over the years, and several pairs of Chisos, but these are by far my favorite. They’re unique, elegant, and timeless. If you’re looking for something that combines luxury with authenticity, these boots are it.

Admittedly, I was pretty nervous about ordering these special boots online, but Allison was so helpful and walked me through the process. She answered all of my questions and concerns. After I received my boots they were too tight. So I shipped them back and Will worked his magic. He stretched them out and changed out the insoles. I came into town and both he and Allison waited for me after hours to ensure that the boots fit better. He even pulled the boots off of my feet!! Does your CEO do that?

It goes without saying that we will be back for more boots! In fact, we are in Austin today to do exactly that!