As you can infer from my handle I fall into the very casual zone of kilt wearing. I also just turned 50, which probably makes me somewhat of an exception.

So far, the most I've "dressed up" is a tucked in Oxford shirt and black shoes for casual work days or an evening out to the local pub. I own several suits, a sport jacket, dress slacks, etc. but avoid wearing them if I can - just not my thing. However, I would dress up if I were going to an event that required it. Not because I would care so much as I wouldn't want to embarrass anyone or cause offense. It's just part of the social contract.

Many of the gentlemen here dress very sharp. I respect their commitment to tradition and have been learning much from them. Who knows, as I grow older (and perhaps wiser), I may change my mind. Along this line of thinking, I'm sewing a casual same-backed vest to wear with my kilt to give me more flexibility. Oh, and a pocket watch - must have a pocket watch to go with the vest ;-)

So, I say wear what you want how you want. If you and the people around you are comfortable, then you're dressed appropriately. I don't think at the end of my days I'm going to look back and think "I should have dressed up more". Any more than I will think, "I should have worked harder". I'd much rather work to live, than live to work. Being comfortable is more important to me.

Just my $0.02