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If you want work boots look into Thorogoods.
$120 for horween leather(same as redwing but not as good clippings at times), goodyear-welted(ability to take to a cobbler for a resole, any welt is), almost no break-in period(comfy out the box).
Then just use Huberd's Shoe Grease or Obanauf's leather preserver to waterproof the leather.