I've worn hiking boots and now wear a pair of 8-eyelet Doc Martens that are getting pretty worn out. Going back to hiking boots, since they're more my style and are a bit more comfortable. They also provide better ankle support than the Docs do. Anyway, with boots, I'm going to dissent a little from what Ham does and say that I prefer to wear my kilt hose fully extended. Looks better, especially if I'm wearing darker hose (or other dark-colored socks)... If you're thinking of cowboy boots, they may not work too well with kilts.

Oh, btw, Atticus, the boots that are worn by the UK model, are New Rock boots, IIRC.
-J