A Brief Yet Fascinating History of the Word "Pretty"

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Stocksy/Javier Pardina

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.

But… was it always? And if not, how did this seemingly innocuous, two-syllable word acquire so much semantic baggage? To answer these questions, we consulted language authorities to chart the etymology and history of the word “pretty.” Here’s what we found: