Well for me, i live in/near the mountains nowadays and have backpacked/climbed for so many years that my choices are skewed toward a boot which will support my feet/ankles while i'm carrying a pack.
My latest boots for Spring/Fall/Early Winter are here - Alpina "Peak" boots. Nothing like the superb quality of full-grain, 3mm Perwanger leather!!!:
Alpina - Peak
They're probably not available in the States anymore, but i live very close to the country they were made in. Oh, and i got 'em for about $125US!!!
For when the temps are gonna be cold, i use an insulated mountain boot. Found here:
La Sportiva Nepal Extreme review by MissionsMan - Trailspace.com
They're not the current model - see the price i paid for 'em - what a SWEET deal i got - could not believe it!!! I've had 'em for along time and they're still in excellent shape (could do with a re-sole of the Vibram though).
If it's gonna be really freakin' cold, i wear these overboots/gators, well, over my LaSports.
WhittakerMountaineering.com -- on sale, footwear, outdoor research, brooks ranger overboot
They're ready to go for arctic wear - no joke. I've had my feet frost-bite more than a few times and now they are almost always cold. Even in summer so i really need something warm that won't let me down. The boots and such i wear really perform in harsh conditions - as in -25F standing temps while cramponing into hard snow/ice - very cold stuff.
Granted, my choices are nowhere near the standard "hunting mans" boots. I used to be that guy - grew up in dairy country, but i somehow found myself heading to the mountains - something bigger than the Porcupines (for the "Yoopers" here!). Now, my choices are radically different and conventional "hunting boots" aren't remotely in the same league. Those types of boots are still good, just nowhere near as capable.