i have crockett and jones cordovan chukka boots with a dainite, and it is a wonderful combination!
pairs wonderfully with my suits and beautiful with raw denim as well.
they are great for when there is shitty weather outside, though its a little heartbreaking when they get scratched up.
very little maintenance, and they keep your feet very warm and dry,
i think you will be very happy with this investment for a long time, as long as you choose a style that is classic and versatile.
i do think that getting anything but boots in cordovan is a little bit of a waste as it kind of defeats the purpose if you're trying to weather the rain with cordovan penny loafers...