I mostly wear sneakers and Chacos with my kilts. I only wear other shoes if I'm "dressing up" a bit. I just wear what I'd usually wear anyway. I wear kilts to be comfortable, so why would I do anything different with my feet?

Flairball, where are you in Boston? I live in Allston, and am happy to get together sometime to answer any of your questions about kilting or hiking.

Andrew.