I am very into comfortable shoes (I will spare no expense) and after trying several brands, I came across a brand called Mephisto (made in France). Nordsrom sells them and so do they in their independent stores. They are legendary in comfort and the choice of the "upper crust" for casual shoes, but they also make a decent work/dress shoe and the pair I have had for over a year now set me back $320 but with 100% goodyear welt sole and top quality construction (rare these days) they still look like new. Also, when the sole wears out, they will recondition the whole shoe and re-sole it for $70 at their Ontario, CA location. Just mail them in.
Next time you are at a Nordsrom, go in and try a pair on, you'll be amazed.
They also have a great low key look for the most conservative uniform regulations.