I've enjoyed substantial in two careers that probably lie near the extremes in this debate - IT and the military. Here's my 2 cents:
What is considered an appropriate appearance is relative, of course. No need to get into a long analysis of the why of it, suffice to say that dress norms and faux pas change over time. You can look it up, there is plenty of interesting analysis out there. Why do we shine shoes? How did the neck tie come to be a marker of professionalism?
That said, IMO, appearance matters, in that it shows an attention to detail. The norms may be arbitrary, but that is irrelevant. The fact that you put some thought and effort into meeting them (or intentionally flaunting them), says, on the whole, something about your character. Are you able to conform to a rule system when someone (that is not you) deems it necessary?
As a GUI designer, appearance and presentation are highly important in my work. Believe me, there are plenty of arbitrary guidelines for MS software out there (e.g. ribbons); there are also plenty that are functionally justified, or simply based on aesthetic principles. Sometimes the standard presentation is assanine, but it is the standard. Most industries have the same mix, I dare say.
If it is not in someone's manner to apply, modify, or disregard these rules as appropriate, then I would posit that they may lack a certain ability to read nuance. That is, if you consistently show up at work looking like 10 pounds of sh** stuffed into a 5 pound bag, your bosses, co-workers, and subordinates will unfortunately be hesitant about your ability to do your work and do it well. They may even think - (s)he doesn't really give a d***. Unless perhaps your work does not require you to exercise any sort of judgement.
And yes, perhaps in the millenium generation's world view, jobs that require any sort of "playing by the rules" are archaic and will have no place in the new world economy. Until we're there, I'll keep my working shoes looking well-cared for. I'll probably also scuzz about my house in my beat up sandals and shirt with semi-vulgar slogans.
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