I've been wearing a pair of Cruiserworks shorty side-zip boots for 5 years and 50K miles or so, and they are still waterproof and look good with normal care. The soles and heels are a soft compound that has worn down, and they shrank just a tiny bit after a bunch of rainy rides. So I would recommend going up a size from your regular shoe size if ordering. ....
I have close to 1000 miles on my Cruiserworks boots and like them a lot. I bought them after hearing a long interview with the North Carolina family that runs the company on Side Stand Up.
I liked that they are made in American sizes for American feet. They really look good, and I also frequently wear them to work.
The only problem I've had is that the heal material melts quickly if you touch your exhaust pipe with it.
The side zipper model like I have probably does not provide as much ankle support as the lace up version.
They'll resole them for (IIRC) $60, and they told me when I bought them they said that they usually need resoling every five to ten years.
They do stand behind their product.