I have a fedora of sorts--thanks to my 5 year olds fascination with Indiana Jones and his insistance that we have matching. I do not think I would pair it with my kilt. However, if I did it would probably only be while hiking some trails or something similar. I generally don't concern myself with fashion while hiking, so the full brim would serve a very functional requirement to keep sun off my head, neck and face. Whereas the kilt would just be for comfort while hiking. In that case, it may not look good to others but I'm not out there trying to be a fashion model, just trying to get some exercise, fresh air and enjoy the beauty of nature.