Thanks, Zardoz, I had trouble finding the post that got me thinking about it. I guess you were talking about the traditional kilt, and I was thinking about the contemporary kilt.

Basically, yes, I wear the same footwear I do with trousers and shorts when I wear the canvas kilts. I don't ever wear cowboy boots, or any boots that aren't low cut; no special shoes with kilts. The socks or hose might be different, taller or longer/thicker, though.
In relation to shorts, I am putting on the canvas kilt instead of shorts, but it's not really the same.
I am sort of putting on hose or tall socks instead of jeans or trousers.
The kilt is kind of a "different beast" to me too, I guess.