For those few us us who have not always worn a kilt, it might be good to analogize to trouser-wearing equivalents, as others have done. First, though, I'd like to echo what others have said about being overdressed. It isn't that it's too traditional, it's just too much. And sure, it is easy to fall into the trap of dressing like a picture- a picture from an outfitter's catalogue or from the web, or from some costume designer's notebook. What looks "cool" may simply be flashy- There is a highland dress equivalent of a white dinner jacket, but also of a white suit of tails. One can be appropriate under the right circumstances. The other one can, too, but only if you are a bandleader or a competitive ballroom dancer.

But back to CMcG's most interesting question. Too Traditional might simply mean out of fashion. I don't see a lot of comment on lapel widths or the like in THCD discussions, but that is what makes a 70s suit look like a 70s suit and not like a 50s suit. When something is so out of fashion as to become theatrical, well, that might be Too Traditional.

One of David L Pope's many excellent points that I particularly agree with is the idea that being right sometimes puts us in the minority. And sometimes you have to wait on the rest of the crowd to catch on, if they ever do.

Finally, this leads us to the "if you had spinach on your teeth would you want me to tell you" problem. I tell my brother and my childhood friends not to wear white hose. I would not tell my boss, if I had one, and if he wore a kilt. And I would not tell my future father in law, at least not on my first date. Wear the pleats at the back, yes. No white hose, ... naaah.