For the past 8 years, my consistent, almost-every day choice of footwear has been the Blundstone BL 063 boot in black, AKA 'The Cuthbertson'. Blundstones come from Australia, though they're made elsewhere now, and the company has been around in one form or another since the late 1800's.
My preferred model is their 'dress' version of the boot, with a more chiseled toe, and a leaner look. Since I've started wearing them, I've bought other boots and shoes, but keep coming back to my Blunnies (as they're known). Mainly, this is because I walk to work and back every day (and also walk almost everywhere else I go), and nothing is as comfortable as these boots. After a year or two, they tend to wear out, and I have to get a new pair. The toebox stretches out a bit after wearing them for a long time, so they look a little less pointed (at least to my eyes), but in general, they look good for as along as they last, as long as I polish them every once in a while.
Now they've introduced a stylish brown suede version--very nifty! I plan on getting a pair this spring, in time for the end of the rainy season in Seattle.