One of the Coolest Hats Ever, And You Probably Won’t Get One: Kentucky Boy Tyler

Are these not the coolest hats you’ve ever seen? Welp, as cool as they are, you probably won’t be able to get one.

If you care about craftsmanship, quality and care, please go buy some clothing from Kentucky Boy Tyler. Tyler has slowly become one of my favorite designers of our generation. I was first introduced to Tyler back in 2018 when I was first learning to sew. I was obsessed with the artisanal, hand sculpted quality of all of his products, particularly his sashico-esque stitched hooded bomber jackets and denim pants. The amount of time, dedication and care that went into each of these products made them that much more special. His pieces feel more like an art piece rather than a piece of clothing. Tyler finds a way to create without contributing to giant, overproduced mess of garbage produced by large fashion corporations. It’s hard to come by products nowadays that have a similar level of care, so if your question is about the quality, it’s a no-brainer… buy something and see for yourself how great it is.

$165 for a hat seems like a steep price point… right? So is it overpriced? Hell, fucking, no. These hats are genuinely one of a kind… each hat being individually sun faded, distressed, with intricately designed materials throughout. Some of the hats feel particularly close to home to me… I grew up going to a surf town in Rhode Island, where everyone wore 10 to 20 year old dad hats (and would pass them down to their kids), paired with shell and beaded necklaces often worn around their necks. How often do you come across a piece of clothing that can hold such a story in such a small thing? Not very often… it’s one of the reasons these things are almost all gone. So, are they worth the price? 100%. No doubt in my mind.

Sadly, I had hopes of picking up Westy Cap #12, but it was gone before I had the chance to click buy. It featured a grey, hand-waxed canvas faded to perfection, hand-beading, and a hand-sewn front patch. Bones from a buffalo were strung together along the front rim, with a removable feather attached to the back. It also had tassels hanging from the back of the hat, the only one in the collection with them. The colors, textures, and shapes all worked together effortlessly. So… it’s off to the after market where I will struggle to find it, because most people who buy from him, don’t sell what they bought. And that tells you a lot about the community and love behind Tyler Webb.