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Without a doubt the best quality and most durable boots are Wesco's. I wear my boots all day every day and ride nearly as much as you and I wouldn't wear anything else. They are very expensive at first, but are way cheaper over time because they are so durable. Wesco can not only resole them, they can rebuild them for about half the cost of new boots.
They offer both stock boots and will also completely custom make a pair to your measurements and specs. I have a pair of the 18" high Boss models which look like this:
HD boots are made by Wolverine (same company that made Hush Puppies years ago) I just bought a pair last week and the tag says "made for HD by Wolverine". Not sure if all the HD boots are made by them, but the pair I bought was.
HD boots are garbage. They look nice but don't last. I just picked up a pair of Redwings. Chipawa makes a nice boot too. The HD boot has cardboard heels with vibram screwed to it...junk!
I bought a pair of HD Gore-Tex boots (made by Wolverine) on sale 4+ years ago when I bought my bike. Wear them year 'round and they are always dry, and not hot in the summer or cold in the winter. Bought a second pair a couple of years ago on a ridiculous sale. Neither pair is close to being worn out (and despite using the toe shifter only, show no wear at the toe), but the original pair will get resoled later this year, after 50K miles. I have no experience with the other brands mentioned, but I doubt I'll be buying boots any time soon.
I also love the red wings. I wear the work boots every day and a pair lasts me about about a year and a half. bought the motorcycle boots, 20,000 miles and look brand new almost. good luck.
Allways ride with cowboy boots, when the sole wears out i get um' replaced with rubber ones for super cheep. Never had water in my boots, the only thing about cowboy boots is there is NO grip whatsoever but rubber soles help all that.
I wear Army Gortex, waterproof, and can go all day in them as I have many times. After wearing Army boots for 23 years, they're the only ones that seem to fit me perfect, go figure?
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