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I'm a commercial/residential general contractor and have blown through dozens of boots. I've settled on Thorogood's as they've lasted the longest for me and are the most comfortable when paired with nice insoles. The classic style boots don't have the best ankle support, however their insulated boots have incredible impact and ankle support. Pic related is the pair I've purchased several times through the years and they've remained waterproof up until I accidently step on a nail or puncture the side/toe. The waterproof line ranges anywhere from $180-$290 but it's well worth it.
