I am now confident and not self conscious in my kilt in Scotland and people are very friendly and pleased to see the kilt, even when they hear my English accent. It is more common to see them in Edinburgh (and quite rare in other areas), where it seems quite common to wear a kilt on a night out that is not a special occasion. Old ladies are particularly encouraging - one nice lady told me that you can wear it "absolutely anywhere". However climbing a Munro kilted in the winter months is not a great idea. Something suitably long and waterproof is a good idea.
John
PS I believe I have seen the gentleman in Inveraray on a very wet Sunday in June when I was buying maps. You are an asset to Visit Scotland!