I've actually thought a lot about this question. Being a 28 yr old musician/writer stuck in corporate hell a lot of the responses here don't really apply to me. I've used many of the more glib responses but after really thinking about the question I realised I wear kilts because it's a part of my identity. While I'm not 100% scottish I can trace my family on my mother's side back to clan MacDonald so that's the tartan I wear and being a believer in celtic spirituality (I'll leave the religious debate there) I just really believe that for the most part people spend their lives looking for their place in the world. Their "tribe" if you will. Wearing kilts is my way of honoring my past and the "tribe" for lack of a better word that I belong to in the world. Of course I reserve this response for close friends and serious inquiries. Most of the time I resort to, "they're comfortable, so why not?"