It takes a while to get used to it. I was lucky, my brother and nephew preceded me in kilts. But I remember the first time I left the house in one, I was a little nervous, but I just strode out like I was in total charge.

A lot of feeling comfortable is "psyching" yourself into an attitude that what you're doing is perfectly normal (it is) and going about your business.

Also, I would recommend reading some of the threads about how to answer questions and comments about the kilt. I had a few of them ready to respond with and was able to sound confident when I did get comments. That made me feel better prepared to go out in my kilt.