The first and most important item in achieving a classic appearance is proportion. That simply means that the elements of your outfit should complement each other in terms of their size and measurements. This would include items like jacket fit, lapels, ties, shirt collars, etc. that can be variable, and the width and length of each element. If any one of them is out of harmony with the rest it can throw the whole outfit off. In much of what follows you are going to find me somewhat out of synch with what passes for cutting-edge fashion these days. My advice is to avoid it like the plague, but you should make an informed decision based upon what you read here and see elsewhere.
For example, nowadays there is an unfortunate trend towards overly skinny lapels, as though designers are channeling the Mad Men television series. The first problem is that look was peculiar to the era circa 1962 and does not translate well in today’s world. Keep in mind that following that extreme, fashion went to the other, with super-wide lapels and ties that look preposterous to us now. In the intervening years clothing has settled within some parameters that could also have applied to the years before these two anomalous periods, and which are reliably consistent over time. If men were to go the skinny lapel route they would basically have to trash all their other clothing, in which they probably have an enormous investment. This is not likely to happen so this particular design choice is probably ephemeral. If you buy anything with lapels two inches or less in width I guarantee you they will out in your next garage sale.
What’s even worse is that they have come up with this jacket design without any adjustment to ties, and especially shirt collars. As a result you get a downright silly look with shirt collars that are too big and ties that are too narrow even with slightly thinner ties. The shirt, tie, and jacket are totally out of proportion and look terrible. Clearly not a classic look.
Another objectionable trend is towards impossibly short jackets that are almost vest-size and end somewhere above or at the butt, (and certain fashion magazines are even promoting this look). But to most people it simply looks like a jacket that doesn’t fit, and if you add some baggy pants to that you’ve got a look that makes Charlie Chaplin’s outfit seem sophisticated. Yet I’ve seen some young men in Manhattan walking around like this and again the overall impression is that the clothes don’t fit. If current designers want to keep raising jacket lengths why not dress like matadors then? If this trend were to stick you’d have to trash all your suits and jackets, which again is unlikely to happen. For a suit jacket or blazer to look right it should cover or nearly cover your butt; personally I prefer the longer variety. A suit jacket is not a sweater or vest and should be nowhere near as short. Consider how a vest is proportionate to a jacket in a three piece suit. That jacket is the proper length. Perhaps they’re trying to put this over to save on material costs, or simply to be “different,” but whatever it is, it is the opposite of the classic look we’re concerned with here.
To save yourself subsequent buyer’s remorse, always avoid the latest fashion extremes. You won’t be sorry and your wardrobe will have a long and useful life. That is of course assuming you’ve stuck to some of the classic guidelines we’ll outline here. One of the first is to carefully select your clothing based on how you look, not on what it costs. A good classic wardrobe is going to cost your more than a haphazard combination of mediocre clothing will, but it is well worth the price difference. Mens fashion is not like womens. The changes are far fewer and less extreme, and the best clothing consequently costs more. Thus when shopping you should be thinking not just how this outfit is now, but how it will be, say, five years from now. You could do worse than look over the past several decades, going all the way back to the 1930s and average things out to get an idea of what is true and lasting. For as with anything you do seriously, the best advice is always to pursue moderation in all things.
Thus the first clue as to a good classic design is proportionate components that complement each other. The combination should make sense in the simplest terms.This is not just a matter of opinion for there is a reason our instinctive reactions to visual elements so often coincide. Ultimately If things do not look or seem right they probably aren’t, and should be bypassed by the man with good taste.