For a grail BIFL - check out JK boots' arctic series.

For loafers (admittedly on the higher end of your price range) is Grant Stone's traveler loafer. I love mine and they have great support.

If the budget is a little tighter, I'd probably go with something cheaper with more foam in it (like Cole Haan, maybe florshiem, something you might see at DSW or Nordstrom Rack).