This is my third pair of Rockports--three completely different styles--and I've been very happy with every one.  They all fit beautifully, require no break-in, wear well, and are fairly priced.

I have very wide feet, and these penny loafers, which I ordered in chili, size 10-2E, fit me perfectly. The toe is very slightly squared, which I think is due to how wide they are; otherwise the toe would have to be longer, which I wouldn't want.  The color goes well with chinos and other earth tones, and I can wear them any time a formal shoe isn't required.  They have an oiled finish that's not polished, so they scratch easily, but the scratches rub away.  I've walked all day in them without any irritation or discomfort, right out of the box.  No break-in required at all, no ankle rubbing. Highly recommended. (Note: if you really want to stash a penny in these, you can't--the classic penny loafer design isn't attached to the toe so the penny would fall right out.)