Joel -
I wore my kilt to Christmas Eve and Easter services last year. I was a little nervous as nobody had ever worn a kilt (to my knowledge) to our church (United Methodist). I wore a tweed jacket and waistcoat, so I was fairly dressed up. As these are "special" services, many men who normally would wear slacks and a collared shirt also wore a coat and tie. I can say I got MANY compliments. One elderly lady came up to me after Christmas Eve service. She was originally from Scotland. She actually got choked up as she thanked me for being kilted, and said she could not remember the last time she saw a man in a kilt. So, you may wish to consider making one of the special church services as the time to make your debut in a kilt. I also think you would feel more comfortable if you made your debut in a tweed jacket and tie.
It also helped me that I am of Scottish heritage and was wearing my family tartan. Many folks asked me what tartan I was wearing and it made me feel good to say, "Stephenson Modern".