If somebody is described as “pert,” that’s (sometimes) a good thing. To be “pert” is to be lively or outspoken. On the other hand, to be “pert” can also be a bad thing. To be “pert” is to be impudent or sassy. In both cases it sort of dates the person using the word, too — usage of “pert” has been declining for the past few decades.
The difference in whether “pert” is a compliment or an accusation, it seems, is the age of the person you’re calling “pert.” If the “pert” one is younger than you are, it’s bad. If they’re older than you, then it’s good. It’s sort of like that joke about driving on the highway: anybody going slower than you is a moron, and anyone going faster is a lunatic.
It used to be easier to discern between the good and bad aspects of being “pert.” And by “used to be,” I mean a few centuries ago. “Pert” showed up in the 1300s, and was probably a shortened version of “apert,” which meant open, public, or unconcealed. It could be applied in several ways. Bold actions in battle were “apert.” Something plainly understood was “apert.” And in only a slight stretch, being expert or clever at something was “apert:” “Ther nas non in al the Kynges londe, More apert man than was he.” (1330)
“Apert” also could be used to mean outspoken, just as “pert” could, but when you were outspoken in a negative way — being impudent or sassy like one of those awful pert kids nowadays, that was “malapert.”
Shakespeare used “malapert:” “I must haue an Ounce or two of this malapert blood from you,” (Twelfth Night) as well as “pert:” “Awake the peart and nimble spirit of mirth,” (Midsummer Night’s Dream), but avoided the older word “apert.” He did, however, use a word that turns out to be closely related: “expert.” It shows up in Othello: “ His Pilate [is] Of very expert and approu’d allowance.”
If Shakespeare had been writing in the 1400s instead of the 1600s, though, he would have had the choice of another older word, “aspert,” which meant much the same thing, but disappeared somewhere in the interim. “Pert” shows up in all sorts of other words, but for some reason almost all of them have either disappeared or are in the process of fading away. English speakers used to have at their fingertips “cockapert” (an impudent chap), “officeperd” (throwing away your work), “pertish,” “pertly”, “pertlet,” “pertling,” “pertlike,” and even “perten,” which was defined in 1827 as “Perten up, for better, more cheerful.”
Instead of “perten up” nowadays, we might say “perk up” — and sure enough, “perk” comes from “pert” too. At least the version of “perk” that appears in “perk up” does. It also means a bird perching on something, and a privilege or fringe benefit. But when it has to do with a bird roosting on a branch, “perk” comes from “perch,” and when it’s a benefit, it comes from “perquisite.” So it’s not really the same word at all. You just have to be pretty pert — or expert — or aspert — to notice.
