When debating the true meaning of a word, one’s first move is usually to look it up in the dictionary. Contrary to popular belief, however, those who write the dictionary don’t define words from a place of all-knowing authority; instead, any lexicographer will tell you their job is to reflect “general usage”—to represent the contexts in which the majority of everyday speakers use a word at the time of its entry, even if that usage is controversial or problematic. So in reality, we all write the dictionary. And as language is constantly changing, a word’s “true” meaning doesn’t really exist.
If someone asked me to define the word “pretty” at this time and place in history, I would probably say something like “a conventionally feminine, palatable sort of attractiveness.” It’s a concept with which I personally have a fraught relationship—in middle school, I had a best friend with long legs, shiny hair, and perfect skin, and we were generally known as the “pretty one” (her) and the “smart one” (me). Later in life, I’d learn that we both desperately wanted to be known as the other. But such is the reality for so many women who’ve been tacitly taught that one can be pretty or one can be smart, but it is almost impossible to be both at the same time.
Type the word “pretty” into Merriam-Webster.com’s search bar and you’ll discover a long list of entries defining every nuanced form of the word, from its use as an adjective to describe a thing (a pretty necklace), a concept (a pretty mess, a pretty penny), or a person (a pretty girl) to its turn as an adverb to quantify something (pretty stupid, pretty ugly). The entry regarding human attractiveness reads as follows:
a: pleasing by delicacy or grace
b: having conventionally accepted elements of beauty
c: appearing or sounding pleasant or nice but lacking strength, force, manliness, purpose, or intensity
Clearly, lexicographers can tell that “pretty” is a loaded term, and when used in the context above, it’s something that many American women both desperately want to be but also resent in the very same breath.
A quick background check on "pretty" will indicate that this word is very, very old (like medieval old) and has taken some drastic pivots and dips since its inception. According to The Word Detective, “pretty” first appears in Old English (so, around 1000 years ago) as “praettig,” meaning “cunning or crafty,” a modification of the word “praett,” meaning “trick.” Linguists postulate that the word was derived from cognates found in Dutch, Low Northern German, and Old Icelandic.
Interestingly, though, “pretty” totally disappears from written recordings for a few hundred years—it skips the whole Middle English period; Chaucer, for example, never uses it—but it surfaces again in the 15th century, now with the more positive meaning of “clever” or “skillful.” It’s not infrequent for a word to disappear from a language then come back again: With “pretty,” Russian linguist Anatoly Liberman theorizes that it may have re-emerged when it did thanks to the thousands of people who were traveling back and forth between England and Germany at the time—the Germans may have reminded English speakers of that old word “praettig” and inspired them to bring it back.
From the 1400s onward, “pretty” acquired more and more definitions, soon coming to mean “elegantly made or done” (like a pretty speech). Quickly, this positive connotation comes to describe things, places, and people. When applied to a woman or child, it meant “aesthetically pleasing,” much like it does today. But British etymologist Michael Quinion says that for a while there, “pretty” could even be used to describe men, either as good-looking (a pretty lad) or as “brave, gallant, warlike.”
Shakespeare certainly used “pretty” this way. In As You Like It, King Lear, and Coriolanus, he repeatedly uses the word to characterize men as physically attractive (e.g., “How now, my pretty knave!”). Shakespeare was a big fan of the word “pretty” in general and used it well over 100 times in his writing, taking advantage of almost every one of its potential meanings from “clever” to “proper” to “good” to “considerable” to “childish or trifling” to “attractive.”
Speaking of Shakespeare, it must also be said that the author and Shakespearean scholar Gerit Quealy is convinced that the word "pretty," which is spelled "pretie" in many old texts, might also be a diminutive form of precious, which was spelled "pretious" with a "t" in its early days. "Diminutive is a key word here," Quealy explains, "because it seems often to refer to something small."
As a compliment specifically, “pretty” weakened over its centuries of use, and by the 1700s, it would only apply to men who were seen as dandies or fops (aka, men were overly concerned with their appearance). The word diminished for women, too. In fact, as early as the 1500s, there was, as The Word Detective says, “an implicit distinction in usage between ‘pretty’ and ‘beautiful,’ and ‘pretty’ was often used in a patronizing or even depreciative sense, especially in the form “pretty little,” still very much in use today. (‘We don’t need to bother our pretty little heads about it.’).”
“In this sense,” comments Quinion, “[pretty] was applied, in rather a condescending way, to young women as a reduced version of beautiful.” Through the years, the negative use of the word for men has almost entirely faded, yet this weaker sense of feminine beauty has more or less remained.
With such a dramatic history, it’s really no wonder why so many women feel ambivalent about being called pretty. To a lot of us, it feels reductive or belittling, yet because we’ve been taught that it’s a good thing for a woman to convey a palatable, youthful form of beauty, we still aspire to it.
The good news is that language never stops evolving, never will, and scholars agree that young women—the very women society wants to be “pretty”—often lead the charge of linguistic change. Whether it’s because young women are more willing to use language creatively or because they’re more likely to see language (as opposed to brute force) as a tool to gain societal power, they are usually at the forefront of new verbal trends. So if you’re a woman who finds herself sick of our current definition of “pretty,” feel free to change it. Twist it. Use it in a new way. Who knows? The dictionary could be soon to follow.