(a topic inspired by some excellent recent threads & posts, ranging from RJMan's recent post on ASW, Manton's pocket square thread, the peacock thread, and a brief discussion in MC General Chat on the difference between "getting dressed" and "dressing up".)
Whether it appears in insanely hyperbolic form as blog-sprezz or in more traditional form as the suggestion that a square should appear carelessly stuffed in a pocket in order to look good, the idea that an otherwise well-dressed man somehow "loses marks" if his evident care in dressing is too obvious is quite pervasive. It wasn't always like this in Western male culture, it still doesn't apply in some of our subcultures, and it certainly isn't globally true.
Why is the conceit of appearing artlessly brilliant so pervasive a concept in the modern interpretation of MC clothing?
My personal opinion is that it may be a reflection of the high societal regard held for individual genius or flair, and aspirations of the others to mimic those who possess it. In a way, this regard for individual panache unifies both ends of the dressing spectrum on here, from the "tasteful" to the "peacock" (the degree obviously differs!) and also beyond this board into the wider #menswear realm. More unhappily, I suspect it may also reflect subgroup distaste for an up-and-comer/outsider/"foreigner" who tries his best to simply do things correctly but can never fit in because he doesn't understand how to break the rules just right.
I would like to suggest that this high regard for insouciance and artless brilliance at dressing can result in a terrible inauthencity of self.
There are probably some wonderfully natural (?"stylish") MC-type dressers out there. Mostly, I suspect, they are now old enough to have grown up in a very different era. I don't really think we have any of these people on the forum currently (at least, they don't post pics) but that's not particularly surprising as the very nature of an internet forum on style would probably not attract such dressers, or at least not for long. We have some here who can put together some very nice ensembles following a consciously codified set of principles, but that's obviously a different subset. The point is that I feel it is quite false/inauthentic to seek to look artlessly wonderful. For example, the polite fiction that even a middle-aged man wearing a pocket square in this day & age just threw it in there (as opposed to specifically deciding to wear a square in order to appear well-dressed) is as ridiculous as an unbuckled monkstrap or upturned collar point. There is such a strong purpose/intent behind wearing any smart tailored look in these informal days that it is always "dressing up" rather than "getting dressed", even within the few occupations that still mandate a suit & tie (after all, we all know what the average guy looks like in a suit & tie).
If we are indeed all just "dressing up", shouldn't we be honest about that rather than trying to ape a different look? Is there not something "cleaner" about simply acknowledging that we enjoy dressing up? Our era is not one where formal tailored looks dominate and where a slight variation becomes the height of elan. It is an era where to be in a tailored look already marks you out as different - it is a very obvious fashion choice - and everything beyond that is simply a matter of what flavour of different you want. You're already clearly marked out as "someone who enjoys clothes" simply for throwing on a jacket, with all the positive and negative inferences people may make around that. In the eyes of the average person, this is probably as true for Foo as it is for NORE, and as true for FNB as it is for Manton, despite all their obvious differences in actual tailored appearance(/modality?). The highwire act of choosing the correct button or buckle to leave undone, or correct fold of square to use, holds no appeal for almost everyone outside of this forum and its associated subculture. These variations are no longer noticed by society at large, unless taken to astonishing extremes (think prom outfit type garishness, or Pitti-blog level nuttiness) because the basic act of wearing a tie has already done the distinguishing work for you in many places.
The one exception I can think of the above is being an employee in a city, profession & firm where a traditional tailored aesthetic still rules the roost. And not just in the fact that there's a suit & tie dress code, but tjat it's an institution with sufficient standards and cultural signficance that a high level of absolutely correct dress is expected. There, the highwire act is restored, and a daredevil puff vs a TV folded square can againbe noticed for what it may once have been. There are precious few such insitutions left, but maybe you can think of some.
TL;DR summary? Just read it, you lazy gits! But I would like to emphasise that I intend no slight to any member or former member and the thread is posted in a spirit of genuine reflection and inquiry, with no "side" or angle to it. I'm interested in hearing what you all think.