I found that wearing it for specific Scottish functions or commemorative days worked well. So I started with my Aunts birthday (she is Scotch), and then moved to St. Andrews day, Burns Night, and Tartan Day. I have found that most people give you a "oh, thats nice" answer when you can give a particular reason that is associated with Scottish History or Culture. After that you just branch out for more and more days (your birthday, "no pants day", kilted Thursdays, whatever).

I found that initially in public, I was much more comfortable wearing kilt hose and appropriate footwear with the kilt. In my mind this helped establish in the minds of those seeing me that I was wearing a kilt and not a plaid skirt. I ditched the white hose for a similar reason (they look like girls knee socks to me) and only wear colored hose with my kilt.

Andy