Alden, Peal and Co., To Boot New York make high quality dress boots. They will start at around $300 and go up but they are made in the U.S. or Western European countries and I bet you can send them to the factory every couple of years in order to replaces soles, etc.
I know, $300+ is a shit load of money but I discovered that it is cheaper to get high quality footwear once and then re-fresh it once in a while as opposed to buying something mid-grade every year. If you know how to take care of shoes, you'll be looking at $100 refreshment service every 3-4 years. Also, stick with leather soles and invest in Galoshes (
http://en.wikipedia.org/wiki/Galoshes).