I think this relates to what is at the heart of the style vs fashion debate. I always associate the idea of "style" with something more timeless--of course tastes will shift, but they will shift slowly, over the course of a century perhaps. Fashion changes at a much more rapid pace.
Within the boundaries of style there is a tremendous amount of leeway, though this is dwarfed by the amount of freedom within the bounds of fashion (treating the two as separate paradigms). The more liberties taken with tradition, the more dated your look will become as time passes(and would perhaps end up within the realm of what some--myself perhaps included--refer to as "bad taste"). This isn't really an issue for fashion types; I doubt they go out all gothninja with the expectation that in ten years time, that same outfit will receive the same reception from their peers.
It has nothing to do with practicality. I doubt anything fashion forward can compete with the utter impracticality of ties and pocketsquares, but ties and pocketsquares are part of a particular longstanding tradition and thus, in ten years, we will look back on most of our ties to find they are still in our rotation.
Some ties take greater liberties with tradition and thus become dated even more quickly. Those ties are among them; I'd posit that they were never in good taste; I don't think most with good sense purchased ties like that in the 90's thinking they would look good a decade or two later.
I was looking at Henry Carter ties and this one caught my eye:
I like it now and may purchase it. But I can also easily imagine blanching at this tie ten years from now.