You do need to take pride in what the tartan and kilt means to you and wear it proudly and I don't think you should defer to people who are annoyed by the sight of a kilt for petty reasons. But you shouldn't feel slighted if someone asks you to conform with a certain vision they might have for a special day.

I don't think it ever makes someone less of man, to display courtesy and deference... in fact I think it shows that you're comfortable in your own skin when you can concede gracefully for someone else's sake.

It's okay to break social conventions, especially ones that are arbitrary, you're free to do it. Just exercise judgment when breaking a convention might hurt the feelings of someone you care about and respect. Having said that, I'm doing everything I can do to make it obvious to friends and family that I'm more often than not a kilted person, and that kilts are not just comfortable and different, but they are meaningful to me. I'm hoping to create the idea in their mind that I'll be in kilt by default unless they have a deeply held reason for asking me not to be.

Where you draw the line can also depend a bit on your community. Savannah is fond of its history, has strong Celtic roots and also tolerates its eccentrics. In this town, I would expect to ask when attending a funeral, memorial service or wedding. Those are solemn occasions and the family's vision should be paramount. But I won't ask when invited to black-tie receptions, fund raising dinners and galas, because here you're expected to strut your stuff a bit, and expected to imbibe more than a bit, and there's no way I won't be kilted on those occasions.

All of which is a long-winded way of saying, manners do matter and Makeitstop's nuanced post highlights why it would probably not be a good idea to have a hard and fast rule about kilt-appropriateness, particularly in the U.S. where the sight of a kilt is still regrettably rare for most folks.