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I've been riding with combat boots for around 20 years.Not those new fangled desert tan ones just regular black leather combat boots.I had a cold weather pair that was totally waterproof but they were also Gortex lined which made them hotter than hell and not particularly comfortable off the bike.They take a while to get broken in and can be downright painfull in the mean time but once broke in they're as comfortable as a pair of tennis shoes and last for years.
I think I went over this before, but seeing as how the USAF is going to a new uniform, with new green suede boots, I've been using my old leather summer black combat ones from my old uniform. If you get the winter version, which are Gortex lined, I would imagine your feet would sweat like there's no tomorrow. If you use the summer version, they are as great as Ed said, not so comfortable at first, but after a while of wearing them, you don't even realize you're wearing them. If you get the summer wieght version, and want waterproof, be sure the whole boot is leather. That way you can spray the leather waterproof crap all over them, and be good to go. By doing this, you may get sweaty feet though too. As you waterproof them, you're also making them non-breathable. If you want, just polish the crap out of them (I'd recommend Parade polish), and then you can wear them to work, and not have to change into any other type of dress shoe... The wax should keep you well protected from the elements too! You should be able to picka pairup at your local military surplus store for pretty damn cheap too (at least a crap load cheaper then what HD or others are charging).
I'm gonna go with the Air Force guy (first time for everything) but I always find a good pair of boots and break them in but I keep them heavily polished not shinny but just allot of carnuba based shoe polish which will repel water all by itself. i personally wear squared toe engineer boots and mine always break in very nicely with time.
Black Danner Winter boots... Great for ruck marching in the snow or riding in cold temps and they are water proof. Not that the navy or airforce would know what a ruck sack is...
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