i don't know if it's just a venerable casual style or if apple's late to the party, but that's been my general mode of fashion since around my senior year of college. and i certainly wouldn't consider myself trendy or stylish. "respectable goob" is what i go for.
in fact, all the articles in the picture are a couple years old, except the pants, which i bought last month to replace a similar pair that had gotten holes in the knees.
oh, and for halloween, my wife is going to be an ipod.