Boots boots boots

[Malachi]

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.

I finally bought myself a pair of Catskill moccs, these are without a doubt the most comfortable footwear that I have ever owned. They can be quite pricey, I paid $ 900 for mine by the time I finished customizing all of the options that I wanted on them. They look absolutely stunning with my great kilt. I have a natural flap at the top of my 10 button moccs (much like what you were asking about regarding the "pirate style boot") and I think that it looks really nice in a kilt.

If I ever get a "round to it" I will take some pics and post them.