Three words: Alden 405 Boot
(Sometimes also called the "Indy" boot.)
It looks like a typical "Red Wing" work boot, until you look just a little closer: the welt is very well done, and is only extended on the front 3/4 of the shoe. Around the heel it's cut close with no visible stitching, giving a subtle sleekness to the boot. The layers in the heel stand out a bit, the sole itself is a cork/rubber combination. It's sort of a "stealth" item: people see it and know something is refined about it, but are not sure what exactly makes it special. IMHO, it looks great with jeans, or with a blue suit in foul weather, or with grey slacks. Very versatile.