Everybody knows what “silly” means: foolishness. To imagine that it means anything else would be just silly. But “silly” is a word with a very long history, and it hasn’t always meant “foolish.”
The whole silly thing begins back in the days of Middle English, when it was “seely.” “Seely” had a couple of meanings. The first was “being on time” or punctual. You can find that sense in this quotation from a manuscript found in Trinity College in Cambridge; it dates from somewhere around 1200 (“seely” is spelled “seli” here): “Ðe ðridde [werke of brihtnesse] is þat man be waker and liht and snel and seli and erliche rise and ȝernliche sech chireche.” In that same era “seely” also meant fortunate or happy (in those days “happy” had more to do with good luck than good feelings): “ The by-tide a cely chaunce, thi lyfe was savede this daye.” In that line, “seely” is spelled “cely” — Middle English had very few sticklers when it came to spelling.
“Seely” didn’t appear out of nowhere (although there are plenty of words that seem like they did, which is kind of silly right there). It came from the Old English word “sǽlig,” which appears in similar forms in a number of old Germanic languages, from Old Frisian (“sêlich”) to Old High German (“sâlig”), and even Old Saxon, which is a language you don’t hear much about, but contained the word “sâlig.”
“Seely” and its immediate predecessors had a third meaning: “innocent” or “harmless,” particularly in the sense of children or animals who don’t deserve the bad things happening to them. In 1297 the “Chronicle of Robert of Gloucester” used the word in this sense: “To þe king of hongri þis seli children twie He sende uor to norisi þat he wardede hom wel beye.” By the way, Robert of Gloucester was a real person who even has his own Wikipedia page. There are two of them; you’re looking for the one labeled “historian” who lived from sometime in the mid 1200s to sometime in the early 1300s. Pretty much the only reason we know about him at all is because of his Chronicle. So if you want to be remembered for centuries (which may or may not be a silly ambition), remember to write stuff down; sometimes that’s all it takes.
Sometime around the 1500s “seely” began to be spelled “silly” (or “sillie” or “silli”…spelling used to be phonetic instead of rules-based and supposedly uniform, but in this realm, as so many others, we’ve now submitted to our software overlords). For a couple of centuries thereafter, “silly” was used in a number of ways, from defenseless (particularly in relation to, for some reason, sheep), to insignificant or valueless (particularly in relation to, for another silly reason, soil), to flimsy, as in a reed compared to, say, an oak tree: “When as the lofty oake is blowne downe, the silly reed may stand” (Robert Burton, “The Anatomy of Melancholy”, 1621). “Silly” was even used to mean “plain” or “simple”, such as something used or possessed by a country peasant.
Our modern usage of “silly” as “foolish” or “frivolous” may have made an occasional appearance as early as the 1600s, but didn’t really become the dominant sense of the word that it is today until the 1800s. One problem with tracing the usage of “silly” is that it can be difficult to tell exactly what a writer might have meant because the context was often…well, it was silly, is what it was. When Abraham Fleming wrote “Wee sillie soules, take the matter too too heauily,”in “A Panoplie of Epistles,” in 1576, did he mean defenseless souls? Harmless souls? Simple souls? Foolish souls? It’s probably a silly question, but that doesn’t make it any easier to answer.
Usage of “silly” has narrowed down quite a lot in recent years; from a dozen or more meanings in the past we’re pretty much left with just two. In addition to “foolish,” you’ll often see “silly” used in the sense of being stupified or dazed by something — you can say someone is “knocked silly,” “scared silly,” or in the case that you notice someone (or find yourself) reading etymological trivia, “bored silly.”