I think I've said something similar to this before, but I believe the attraction of the Trad ethos and rules and curriculum and all of that is simply the fact that there was a group of guys interested in clothes whose taste tended toward the traditional, fogey, old-fashioned, etc., but the look had not been authoritatively articulated before (outside of the satirical OPH).  It had some relationship to the eighties "preppy" fad, but that wasn't quite it.  Harris came along and very succinctly summed up the salient features and gave it a name.  Historically valid or not, I imagine it was a big "eureka" moment for a lot of AAAC members.

The mistakes, lapses in taste, and all of that spring, I feel, from enthusiasm and the thrill of exploration.  Baggy GI pants and slim Ivy 60s jackets pair poorly together, but they emanate from a common "Americana" aesthetic core, so it's natural both appeal to the neophyte trad.  A sense of what works and when--the nuances--can only be mastered after a lot of trial and error.  David has been a serious student of the look for many years--it's no wonder his understanding of it is more sophisticated than a guy who just knows he's always liked Brooks Brothers and LL Bean and is suddenly exposed to all of this information.  Mistakes are made, but they're harmless, and necessary to the process of forging a personal style.

The aspirational social elite stuff, when it occurs, is grating--but doesn't everyone play dress-up, to some extent?  Is affecting a WASPY elan any more obnoxious than assuming the mantle of a corporate master of the universe, or sexy young urban hotshot, or gangsta, or bespoke addict?  These can all be done poorly or well, and all are, to a degree, based on make-believe.  That's much of the fun, right?