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STYLE. COMMUNITY. GREAT CLOTHING.
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Having read some books on the topic of "cool" I can tell you no one has yet managed to really grasp the subject sucessfully.
I agree with a lot of your observations in the earlier paragraphs. Regarding different nationalities, if I may be equally permitted a bit of deliberately cheeky oversimplification/stereotyping, I'd suggest that the best-dressed Italians dress like they want to be a well-dressed Englishman (filtering that look through their own culture, obviously), and many of the better-dressed Americans (Ivy-stylers excepted) and Asians dress like they want to be a better-dressed Italian...
As many soldiers will attest, if you have to wear a uniform, the little ways of personalising it - within regulations - can have their attractions, including showing you don't take it that seriously. There is a time (state occasions, big parades) for identical perfection. At other times, there is a natural human impulse to show some individuality.
As a former art historian, I find it useful at times to think of MC clothes in terms of artistic styles. There are classical styles, but also neo-classical - the latter inspired by and emulating the former, but not slavish recreations of what has gone before. There are in-your-face baroque styles, quirky knowing mannerist ones (much sprezz seems mannerist to me), and modernist and post-modernist approaches. Of course it doesn't map across exactly, but it does give you a different frame of reference.
There are specific and distinct cultural reasons why insouciance (which is absolutely the correct word) has a powerful hold on ideas of traditional men's style. Mostly from English, French and Italian cultures, as they were the primary drivers of MC in the early/mid 20th Century (and like most such drivers were then swamped by, reinterpreted by, and absorbed into US culture). A mix of an aristocratic "I am a superior person of independent means and higher sensibillity and do what I like", English "don't look like you are trying too hard, or care too much", individualist posing "I am an artist" and so on. It's sort of Beau Brummell versus Lord Byron, and that duality exists in most of us.
What was yours?
A combination of the last few replies touching on the subjects of "cool" and "individuality" led me that there is a much easier explanation of the many sartorial messes: individual style becoming mostly divorced from any meaningful historical context, which makes the whole concept virtually an oxymoron, and that's why (obviously, a pure, though marginally informed, speculation)
First, the whole concept of "style" is virtually meaningless except in relation with specific historical circumstance: to have any notion of a "correct" style (doesn't matter if it is at the individual, class, or society level), there needs to be some sort of backdrop to assess the correctness against. This of course is not, and cannot be, any notion of "timeless" aesthetic principles. It can only be some constellation of norms and symbols reflected or alluded to via clothing. In short, in any period, clothes represent the dominant "mood" of the times - and the common reactions against such mood.
Which brings us to the concept of "cool". While yes, it is virtually impossible to define it at a sufficiently abstract level, many researchers would agree that it can be traced to disguised defiance of authority in the black community: since it was (and in many aspects still is) virtually impossible to oppose whitey without extreme consequences, the "cool" factor is a way to give off a vague defiance without openly confronting authority.
Of course, that's exactly why cool became so important for juveniles of all ages in the 20th century. For those not having to suffer true repercussions, it was easy, it was fun, and it allowed many opportunities to experiment. But not haphazardly - the cool fashions of every decade are fairly identifiable and quite rigid - perhaps because the things to rebel against changed. A big problem for "cool" was/is also the fact that it is extremely easily and quickly coopted by the establishment - and the "proper" cool jawnz are promptly sold back to the would be radicals at crazy prices. You know "cool" is dead when AdBusters market their very own ******* sneaker. WTF.
However, as time went by, these things to rebel against were becoming far less personified and far less obvious at a level of individual fashion symbols. For example, the suit may have symbolized some real power back in the day, today it can be the symbol of a Verizon salesmen, or, if sufficiently crazy expensive and extravagant - of an international playboy. Big confusion here. Either way, pursuing the way of the suit provides no apparent identity if it is done seriously, and there is no way to do it "correctly" if it is not pursued seriously.
There is simply no fashion summary of the spirit of the times these days, so there is nothing apparent to aspire to or rebel against fashion-wise. All that is left is irony. But irony without purpose, cause, and object is simply self-indulgent and inconsequential vomit, as apparent on many sprezzy pics. Hello fashion post modernity.
So, if it's not real irony, then what? I have 2 contradictory guesses: 1) that no overall "rennaisance" in men's clothing has taken any place at all. Just because marketing machines and the fashion industry overhype #menswear in a fight for the dollars of the small proportion of the population that.... has them, doesn't mean AT ALL that on average there is more #menswear in the wild. 2) the middle class is terrified of being "proletarized", reduced to #workwear by necessity, and thus spends a disproportionate amount of effort to keep up the charade. This can go either way: a) "I am real serious dude who knows the rules" or b) i have teh moneyz and can sprezz it up without worrying any time. Both sad and pathetic.
Now, where is individual style to come from? I don't know. But if an authentic individual is to come up with one, I am increasingly convinced that it must be basically a personal uniform: the same or very similar stuff /format every day. Not the faux-nobility with jawnz for "every occasion".
I used to mildly make fun of :foo: , but if the above ramble contains the smallest insights of relevance, :foo: is teh man,
Abandon your quest for sprez, and the rules (snake oil) salesmen. Find the specific persona you are or want to be, and then stock up on OneEverything. No, scratch that: make that just one pair of OneEverything, and rock it until it is ratty and awesome. Then just keep rocking it.
Quote:
Quite off-topic and I can't remember whether I already recently discussed this here or elsewhere (probably elsewhere), but this discussion reminds me again of the Asimov short story, The Last Question. It's quite an amusing little read if you have a spare 10 minutes.
Second, there is a powerful sense of long-standing in Western culture, and still present, that in order to break the rules successfully you have to know what they are first - in literature, music, art, architecture, for example. Insouciance in clothing is the same thing: you are saying "yes, I know I shouldn't have that button undone, or that sloppy PS, or the back end of my tie poking out, but I can precisely because I know that I shouldn't, and you can tell that I know that because I am wearing a beautifully fitted suit and exquisite shoes".
To know the rules signify's that at one point you cared or studied the rules, basically you "soucy" or worried/thought about the rules. That's not cool. Cool doesn't worry ever, it just does it.