With time more diverse kilt wearing

[Chef]

Anyone else notice that over time you tend to get more casual, and have no problem going out in public in a more casual fashion?

No.

I have been wearing a kilt for over 40 years. Casually (not as casually as some), for business, and for formal, but I would never leave the house without a sporran, I have never worn crew socks and sneakers with a kilt and I don't think I have worn a t-shirt with a kilt more than three or four times in my life. However I am very comfortable wearing a kilt and always have been. I don't think you can equate how comfortable/confident someone is with wearing a kilt with how casually he wears it. I don't think a proper kilt is that casual a garment.