Holy Smokes I can't recommend these guys enough.
http://www.catskillmoccasins.com/
They are custom molded to your foot and calf. Will cost you a little bit, but will least forever. One of the guys at our last kilt night in Dallas was wearing a pair he'd had for 12 years and hasn't needed them to be resoled until this year. The leather is breathable, no wearing of socks, the foot is lined. They are completely machine washable. In fact it is recommended to wash your shoes once a year.

I will be buying a pair next ren faire season. The pair I tried on was the most comfortable thing I've put on my foot.

Sorry sounds like I'm advertising for them, but really they are truly a great shoe and have been used in quite a few movies.

Medieval Moccasins are also good. Not as sturdy of a sole, but easily replaced.