Q From Barbara Storm: I am trying to locate the origin of the word pretty and its early usage. It apparently had a different meaning in early English that is unrelated to the way we currently use it.
A That’s correct. It is first recorded in Old English, when it had the sense of “trick, deceit”. Then it disappears from the recorded language for some centuries, turning up again in the 1400s in a variety of meanings, none of them exactly equivalent to the Old English form. It could mean “clever, artful”, or “something ingeniously or cleverly made”. And it could be applied to a man, as “brave, gallant, warlike”, which weakened down the years until it was used in the eighteenth century in the phrase “a pretty fellow”, meaning a swell or a fop. But the word also existed in a weakened sense, very much like our modern nice — pleasing or satisfactory in a vague sort of way. In this sense it was applied, in rather a condescending way, to young women as a reduced version of beautiful.