‘Silly Sally’ is a nickname I’ve been assigned since childhood – not only because it is euphonious in its alliterative assonance but, alas, because it’s often true. Like many words originating in Old English, in this case in gesaelig – “happy” – from sael (happiness) – which developed sideways out of Old Norse sels, meaning “good” and “kindhearted” , silly came to mean exactly the opposite.
The Online Etymology Dictionary explains:
“The word’s considerable sense development moved from “blessed” to “pious,” to “innocent” (c.1200), to “harmless,” to “pitiable” (late 13c.), to “weak” (c.1300), to “feeble in mind, lacking in reason, foolish” (1570s). “
Again, around 1570 (see several previous entries) a perfectly lovely word with positive connotations metamorphosed into something negative. If one considers the frequency of this etymological trajectory, which culminated with the publication of Robert Burton’s Anatomy of Melancholy in 1621, it seems that the latter quarter of the sixteenth century was one in which man discovered some darkness of spirit which he anaesthetized etymologically by categorizing, often negatively,characteristics and dispositions – thus the blessed ‘silly’ became “foolishness.”
That this notion of silliness should have been birthed by an existential sadness explains much about Shakespeare’s holy fools and the darkness of Baroque painting.
“The fool doth think he is wise, but the wise man knows himself to be a fool” – Touchstone
Near Depth Experience 