I guess I think there is a fine line between dressing well in a classic manner and dressing in an anachronistic manner. Personally I have many classic elements to my manner of dress (choice of suitings, shoes), but also incorporate quite a few modern ones (shirt/tie color) and some stylistic elements that may have been considered iconoclastic some time ago (loafers with a suit) may be considered at least appropriate and perhaps mainstream. Obviously some rules should be obeyed, but how does one decide which ones? In my opinion, the rules change along with the times, at least to some degree. While there are some stylistic elements that may always be considered "classic" there are some that may go the way of the buggy whip and horse and carriage.
You make valid points (that last buggy whip maker must have turned out one hell of a product). In the meantime, I consider that a simple rule like no loafers with a suit, and I will make that a rather dark, formal suit, out of respect for your well-considered comments, is not in my view anachronistic, it is merely proper, and appropriate, particularly if the fellow doing the wearing is an old guard traditionalist, who deals with others unamused by "fashion" or trends. Regards, Jack