Maybe you've lapped Good Taste, and are catching up to it again.
I've got a "Shrodinger's cat is dead" (with "not dead" on the back) shirt which helps me find interesting people (THE most random people understand it). I'd argue that's more useful than fashion (does it have a use?), and remember that stick-figure shirts occasionally explode in popularity (I remember a big burst several years ago). XKCD is just a superior-taste subset of those.
edit: heck, "fashion" hasn't served me too well anyway. I wore a blue-screen-of-death shirt to one of my interviews, and got the job. The interviewer called the boss in to laugh at the shirt :)
Because part of the point of "taste" is to exclude others, or, if you prefer, to distinguish oneself (which is the same as excluding others). Money helps reduce the uncommitted.