I second the ropers. Got a pair of Justin's for Christmas and I'll never go back. The only negative thing is that they set off the metal detectors. If you look around, I've seen them for as little as $49.99. Can't beat it.
Doc Marten's hands down. I have had 2 pairs over the last 6 years and highly recommend them. The soles are oil, fuel and de-icing fluid proof. Its takes a trip or 2 to break them in but you will swear you are wearing your favorite slippers. I inked out the yellow string with a permanent marker or you can find them with black string also.
P.S. Roopers? Do you wear Wranglers and a nice Garth Brooks shirt too?
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.
Personally, I'm using a pair of Wolverine shoes that I purchased about 6 months ago. Before that I wore out several pairs of Rockports and Redwings. These Wolverines are about as comfortable as they come!
I do add the extra-padded insoles to all my shoes, though. Just for that "Cadillac Ride."