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 being able to feel prefigured by one's accessories.
Since fashion functions not by evolving toward some higher better plane but by simply changing constantly and predictibly, any value judgment made in regards to fashion makes no sense; such comments can have no reference point. There is no "truth" to any criterion -- an assessment can make no reference to any ideal because these are programmed to routinely change. Claims about striped ties or the relative lengths of cuffs and collars merely lionize 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 what guides that systematic process of change, of having a sense of when things must change, to keep those bamboozled by the arbitrary details guessing. Fashion magazines, slavish to demands of their fashion-house advertisers, disseminate the arbitrary shifts with the absolute, ahistorical (and consequently schizophrenic) language that proclaims each new season of 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 amalgams of moribund styles still vaguely remembered. No stable Golden age has ever existed to which terms like classic can apply. What is meant by "classic" and the era it's supposed to designate is always shifting and moving in time with fashion, generally. 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 television commercials).
The people on best dressed lists do aren't there 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 tempting aspirational symbols of leisure class luxury -- e.g., royalty, heiresses; people that we're all eager to emulate and thereby imagine ourselves climbing the social ladder. But the truly rich and powerful don't 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 acquiring the right to dress the rich and powerful and famous -- hence the dresses given away for the Oscars, etc. Never mind the fact that these allegedly best-dressed people have the time and money and stylists to help them look good, which is often a professional requirement (and which should really disqualify them from consideration; if dressing up is your job, if you are wearing a glamorous uniform, have you really demonstrated any special sartorial sense?) 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 the copy written to accompany these lists credit the individuals for the stylishness, alleging it comes 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.