The late Fred Astaire, looking very natty in a double-breasted suit and hat.
I have no good answers for this one. It seems generally accepted that the most elegant and tasteful approach to being what we'll call 'well-dressed' is the most subtle. In other words, keep things fairly understated. There's not too much going on visually speaking. Very much in keeping with the remark attributed to Beau Brummel that runs something along these lines. If people stop and turn to look at you in the street, then you are not well-dressed.
The problem with this way of thinking is that it is difficult to dress well in the early 21st century without standing out and drawing attention since so many men leave the house looking like complete slobs. Combine that with the fact that the mess, also known as business casual, that now holds sway in so many sectors and fields during normal business hours, and you see the dilemma. Unless one is in the menswear industry where, presumably, other men dress well because they enjoy doing so and want to impress each other with their style acumen, a man will stand out most places in 2014 by simple virtue of the fact that he is dressed better than average.
There are, of course, a few professions left where, in general, men are still expected to dress well. As far as I know at any rate. Certain law firms, the financial industry, corporate higher-ups, and so forth. Though I suspect that even here suitable attire for the office might depend on organization size and culture, geographic location, the kind of work done or services provided, and whether or not the insidious virus that is dress-down-Friday-is-now-dress-down-Monday-through-Friday has infected the minds of those at the top.
As for me, I enjoy good clothing -- classic men's attire -- and dressing nicely, or attempting to do so at least. I don't plan on stopping that anytime soon. I am a vain, vapid poseur without a serious thought in my head after all. In the vernacular of other times, a fop. A silly macaroni. A damned popinjay. However, I am also well aware that I probably stick out like a sore thumb on even a fairly subdued navy blazer and khakis or charcoal suit day in my small Midwestern city, and on my small university campus, where lack of regard for occasion is the rule, fewer and fewer people have a clue about what is appropriate, and most guys dress like farmers on a Saturday afternoon. And their Sunday best hasn't really been very "Sunday best" for a long time.
In my neck of the woods, extremely few men wear even sports jackets and neckties, besides attorneys in the downtown law firms, judges, a few doctors, university administrators and trustees, plus a few of the muckety-mucks on the top floor of the insurance giant that is based here. Or even good quality leather dress shoes for that matter. On those rare occasions when you actually spot a suit, more often than not it is black and boxy with sleeves that are far too long.
But reconciling the extremes here seems difficult. I'm really not sure how average guys who want, and see a need, to kick up their everyday style several notches might do so in a way that does not turn heads. It's just one more of the social conundrums of life in the early 21st century I suppose. If you have any thoughts on the matter, please feel free to comment.