The History of the Word Loophole

The word loophole dates to the mid-1500s. It comes from a combination of the word hole and the Middle English word loupe, which refers to the “narrow window" or "slit-opening in a wall" that archers used for protection while shooting. Additional root words include the Medieval Latin word loupa, and lobia, which is thought to be a specialized word from a continental Germanic source, such as the Middle Dutch word lupen (meaning "to watch, peer"). The figurative sense of the word loophole meaning “outlet” or “means of escape” didn’t come into usage until the 1660s, but it still carries this same meaning today.