The history of the word "pretty"

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.