Going back to BlueThunder's original question, I will relay this about myself. I don't regularly wear a kilt, but do wear one every time I pipe, some of the time when I practice, always to highland games, generally for black-tie/formal functions, and occasionally other times.

The first time I wore a kilt in public was St. Patrick's Day. I had wanted a kilt but really didn't know a ton about them, so I did some poor research and bought one off eBay. I didn't know how people would react to seeing me in it, so I figured St. Patrick's Day would be a great time to try wearing it, see what people said and see how I felt. I did the same that year on Halloween.

To OP BlueThunder's point, I wore it those days because id people were @-holes to me, I could pass it off as "well, I'm just in the spirit of the day." Contrary to what I had expected, I got mostly very positive reactions, which is what led to me researching kilts more in depth, finding this site, buying better ones and wearing them more often.

I have since passed that original kilt on to someone who had a similar thought, tried it, liked it, bought a nicer one, and passed the original on to someone who had a similar thought. At this point, that "Halloween Kilt" has influenced and converted at least three people, possibly others who saw me wearing it.

I have worn kilts on Halloween since then, but I think it's always been as part of a costume - rugby fan, David Livingstone, John Jameson (blows people's mind that he was Scottish, not Irish), etc. Again, I've always worn it nicely/appropriately.

To that end, I say that if you are looking for a day to try it out and see how you feel, Halloween or St. Patrick's Day give you a good opportunity to do so with a safety net.

RR