Word Origin & History
mid-14c., "to examine, scrutinize, inspect," from over + look (q.v.). Another M.E. sense was "to peer over the top of." These two literal senses have given rise to the two main modern meanings. Meaning "to look over or beyond and thus not see, to choose to not notice" is first recorded 1520s. Seemingly
contradictory sense of "to watch over officially, keep an eye on, superintend" is from 1530s. Overlooking also was the common term for "inflicting the evil eye on" (someone or something).