We have all seen them in the malls and clubs – men in their thirties and forties trying to recapture the style of their youth. Or, even more commonly, engaging in a vain effort to appropriate “a look” for themselves from one of the seemingly endless and eclectic array of looks (“it” and otherwise) paraded around by today’s youth. A “tragic” sight made all the more so by the fact that many of these abandoned sons of dignity seem painfully unaware of how ridiculous they look.

Of course, irrespective of whether their manifest lack of judgment is a result of simple nostalgia; a desire to make themselves more attractive to younger women; a gross misinterpretation of the insistence, popular in the self improvement literature, that we not simply be ourselves, but our best selves; or even some combination of the three; it raises the important question of age appropriate dress. Albeit, not in the predictable – and I will venture to say somewhat banal and redundant – sense of debating the merits of advocating some sort of uniform conservatism in personal style for all but the young. (So feel free to emit that well justified sigh of relief).

Instead, what it prompts us to do is consider the subject of age appropriate dress in the more important, productive and relevant context of dynamic living; which, when it comes to fashion, centers around two things:

1) a simple and inescapable acknowledgement of the fact that, as much as we may hate to admit it, we are all ageing, and

2) a personal commitment to looking our best at every stage along the way.

Consequently, the question becomes just how one might go about embodying such a commitment? And, quite naturally, any attempt to provide a blanket response or answer is met with an objection that is as obvious as it is well justified. Namely, that outside of broad, general trends, which those of us with more refined and fastidious tastes have no interest in being a part of, what is “stylish” becomes a relatively subjective affair – and in fact needs to be! After all, “the first step in the development of taste is to be willing to credit your own opinion.”

Nevertheless, there exists a simple and useful way to guide or supplement our subjectivity. And that is to begin to think of fashion and the lifecycle in terms of a dynamic spectrum, which ranges from being the embodiment of “youthful style” or “trendiness” at one end through to being an increasingly refined pillar of sophistication at the other. With the idea being to progress along the spectrum as imperceptibly as possible over the course of your life – becoming ever more sophisticated, and hence less trendy (at least in the popularly understood sense), as you go.

And, if you find yourself feeling like this idea has something of an intuitive appeal to it, there is an obvious reason:

It is totally congruent with the way wider-society has been conditioned to gradually alter its perception of, and consequently the way it interacts with, us as we age. That is, when we are young, we are seen as the cool friend, work mate, and free and easygoing subordinate for whom being trendy is almost a natural and expected part of being. As we move into middle-age, on the other hand, and move onwards and upwards in our chosen profession, we become the senior manager or boss whose power, authority, and personal presence command respect, deference, and a visible aura of sophistication to match.

Of course, intuitive appeal aside, in practice thinking about fashion in terms of a dynamic spectrum requires the ability to determine just how and when to alter one’s look. And while for some people this ability is almost innate, in most people it needs to be consciously cultivated and calibrated. Fortunately, if you find yourself among the members of the latter category, so long as you can be honest with yourself, with a little patience, vigilance, and research, there’s no real reason this can’t prove a relatively painless process – especially if you bear the following useful, and somewhat axiomatic, ideas in mind:

First, trial and error are inherent in the concept of calibration. Consequently, beating yourself up psychologically over each and every faux pas you make in the pursuit of a more dynamic sense of fashion and style is as senseless as it is counter-productive. Instead, determine to surmount your self-pity and the unnecessary damage it causes to both your self-esteem and self-image, and to profit from your perceived failings by treating them as invaluable feedback.

Second, missteps on the road to developing a more dynamic sense of fashion and style are by no means unidirectional. Quite the contrary, they can, and all too often do, cut both ways. For, just as we advance through life and ever-so-gradually develop traits that are inimical to the style of our youth, young people who lack the physical maturity, sophistication and presence for certain types of clothing can come off looking pretentious and magnifying their personal flaws. An almost caricaturistic example being the young professionals who try to pull off the solid corporate grey and blue suits in conservative cuts favoured by many of their older counterparts, but somehow end up wearing them too loosely fitted. For, it’s almost as though their unconscious mind is symbolically acknowledging that they literally haven’t grown into them yet!

Third, while your personal motivation for developing a more dynamic sense of fashion and style should extend well beyond a paltry desire to gain the praise and approval of those around you, a steady increase in the amount of compliments and female attention you receive will provide a useful indication that you are on the right track.

Finally, whether you possess an innate ability of think about fashion in this way or need to spend a little time cultivating it, remember to enjoy the ride. After all, over and above the renewed sense of dignity that a dynamic sense of fashion and style can bring to our lives, it frees us to try new things and experience the full spectrum of men’s fashion in all its nuanced glory. And this is clearly a very liberating and invigorating prospect.