For what it's worth, I bough a pair of Calela's "Gentleman's Upland Hunting Boots" about a year ago and have worn them almost every day to work, in addition to camping. They're not waterproof, but I treat them with mink oil and have never had any leakage.

They're not just the most comfortable boots I ever wore, they're the most comfortabe shoe of any kind. There was a short break-in period. They're very light and give a lot of ankle support.

After several bad purchases, I decided I wasn't going to buy boots by mail anymore. I think you actually have to try them on first. It was worth the trip to Cabela's, because they have great service in the shoe department.