If you're going to spend that much, get a better shoe. Get the Allen Edmonds Eastport model.
http://www.allenedmonds.com/aeonline/pr ... 0000001_-1I've got at least 9 pair of Allen Edmonds shoes. I practically won't wear any others unless they don't have a style that works. I've had to get a couple of Sperry's for kicking around in dirt and such, but that's about it.
I think I've got 5 pairs of the Eastport alone. Two pair get left on the boat; one's a beat-to-hell pair suitable for cleaning and bilge work. The other are my 'boat only' shoes, to avoid any street grime. During warmer weather I've got two pair that get rotated (one blue, one brown). They no longer make the blue colored ones, unfortunately. Good thing I've got two pair.
I've also used their recrafting service several times and it's amazing. Provided you haven't utterly destroyed the upper (re: bilge shoes above) they send you back a pair that are nearly indistinguishable from new. I have an extra pair ready to go while any of the others are out getting recrafted.
They're terrifically comfortable, lightweight (compared to others), break-in very nicely and last quite a while. And they survive getting wet. They dry out quickly and look absolutely no worse for it. I can wear 'em all day long and feel no difference taking them off. Compared to other shoes where you really feel better for taking them off. Like the Sperry's, they're a good bit heavier (but not as horrible as Timberland junk) and I'm glad to get 'em off at the end of the day. The Eastports, I just don't mind still having 'em on.
Yes, you could say I like their shoes.