Is there anything more infuriatingly inane than a "Best Dressed Man" list? Not to say best-dressed lists for women aren't insulting enough, reducing a woman's competence to how attractive she's able to appear. Maybe there's a crude leveling in afflicting men with the same insecurities. But only the garment and publishing industries truly profit from this new equality in feeling prefiguring by one's accessories.
Since fashion functions not by evolving toward some higher truth but by simply, constantly, predictibly changing, any value judgment made in regards to it makes no sense, has no reference point. There is no "truth" to any criterion -- an assessment can make no reference to higher notions of idealized truth or practicality or rationality or anything. Such claims about striped ties or the relative lengths of cuffs and collars are simply lionizing a random point on an always-spinning wheel. But in truth, trying to master the details of fashion is never a matter of learning specific details and pointers like the ones adumbrated in Best Dressed Lists, it's a matter of understanding that systematic process of change, of having a sense of when things must change, to keep those fixated on details guessing. The magazines, slavish to demands of their fashion-house advertisers, then disseminate the arbitrary shifts with the absolute, ahistorical (and schizophrenic, as a consequence) language that proclaims these new ideas as eternal truths that everyone has just been too dim to perceive before. If there is reference to the past, it is to "classic" and "timeless" looks which are anything but, as an entirely new look has been chosen to be so designated. There is no stable Golden age to which terms like classic can apply to. The classic era is always shifting and moving, too. And of course the compulsion to be classic is joined with a contradictory admonition to look contemporary, or modern; or to look modernly classic, or classically modern. The incoherence of this advice is the key to its efficacy -- you are being encouraged not to think rationally, but to revel in the confused fugue state brought on by irrationality, which pleases the consumer because it makes it seem like anything, no matter how absurd, is possible (just look at beer commercials or truck commercials on television).
Of course the people who make best dressed lists do so not because of their sartorial aplomb, but because they have effective PR people and they are promoting some new film or record, or they effectively serve as symbols of a desirable leisured class -- royalty -- that we're all eager to emulate and thereby imagine ourselves climbing the social ladder. But the truly rich and powerful don't really care how they dress, as their power draws from real sources -- actual land and wealth and social connection. They'll cooperate with the fashion industry, because it affirms their power and invests them with further social capital, but they would survive without it. But the fashion industry needs them to serve as stimulus to their lessers, so they invest a lot in gaining the ability to dress the rich and powerful and famous -- hence the dresses given away for the Oscars, etc. The reason why the best dressed look "good" is because they are selected to before the fact and dressed in whatever style the fashion industry needs them to adopt, which is then touted as the superlative style. We know it's good because the rich, famous guy is wearing it. Exposed to this kind of thing often enough, that even the tautologous reversal that we know he is rich and famous because he looks good begins to take hold.
What's so infuriating about all this is how in these lists the stylishness allegedly evinced is supposed to come from innate personal qualities and smart fashion decisions within anyone's grasp, rather than being the product of an enormous industry apparatus coupling itself to the long-accrued prestige of the privleged classes. The habitus of the rich is beyond most people, no matter what brand label they buy, because that aristocratic bearing is the product of an ingrained sense of entitlement that one must be raised with to feel, and to have animate unconsciously the gestures with which one moves through the world. But these lists obfuscate that, and encouage you to feel bad that you lack this natural grace, and urge to buy more crap to try to get it, a move which will inevitably fail, make you feel worse, and more vulnerable to the same pitch to buy more crap the next time. The point: "style" is never personal. It is always socially produced, and never within one's individual control.