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It may or may not float your boat, but Grapevinehill has the AE Fairfax for about $120 shipped (with their 20% off discount in place till 12/31). Here is a pic:
I agree that the Wilbert is a nice shoe for khakis, but that it wouldn't be appropriate for gray flannels. I don't have any personal experience with Loake, but my understanding is that the quality of leather isn't that great--even at their top line.

The A-E Fairfax isn't a horrible-looking shoe, in my opinion, but I'm not sure if you'd get much mileage out of it for khakis/flannels. This is a photo I took of mine a couple years ago:

My recommendation would be a suede tassel loafer. It will take you from khakis to flannels and back again.
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