@proedie @riley after obsessing a little over getting to the bottom of this, the answer seems to be that the historical origin (from 1711) is akin to "If you stop chasing trends you will sometimes be fashionable", which is more in line with riley's definition in the OP. The other "official" definitions I've found seem to follow this as well.
The definition that "coincidental correctness is worthless" seems to be a personal (though common) interpretation.