Well, after talking with the boss (my fiancee) I guess this Halloween I'm going to surprise everyone at work and NOT wear the kilt! We're having a contest so I think doing something people don't expect will help edge me toward winning some money (which I will probably use to purchase another kilt! ). I'm trying to brainstorm on what to be though.

I guess my conclusion was that for me the kilt is a daily wear item and not a costume. Nevertheless, if done correctly (as the pictures in this thread have attested can be done), then it becomes part of a costume, so I wouldn't wear my daily wear (kilt + tshirt + boots) for Halloween, but would probably do a historic costume or something very unique like what Riverkilt did, but in the end I don't think I could pull off the Bob Marley kilt!

Thanks for everyone's suggestions and comments.