I went to a private boys' high school, where I wore a jacket and tie every day. In the 18 years since then, I haven't had a job that required business attire regularly—except, oddly enough, one of the two incarnations of my rock band.
I think, however, that it's now time for me to buy a proper suit. Sure, I have some nice jackets and shirts and many good ties, and a couple of decent pairs of pants, but not a full tailored ensemble. I own a tuxedo, but there aren't many occasions for those in my life. I'm thinking of a black or charcoal single-breasted suit with a subtle pinstripe or check-line pattern.
Part of my reason for thinking of a suit is that there are times when it might be useful in my writing career, and it certainly is onstage. However, I have to admit that a significant influence is TLC's What Not to Wear. After seeing a number of slovenly men transformed by snappy suits, I wonder how I'll clean up.
Not that I'm very slovenly, mind you.