Q: I’m curious about how “smart” came to mean intelligent as well as stylish. Which came first?
A: The adjective “smart” has meant fashionable since the 1700s and intelligent since the 1500s, but it’s meant painful much, much longer—since Anglo-Saxon days.
When the adjective first showed up, according to the Oxford English Dictionary, it meant biting or stinging, like the pain from a rod or whip. The verb “smart” (to hurt or sting) appeared about the same time.
The earliest example of the adjective in the OED is from Sermo ad Populum Dominicis Diebus, an Old English homily: “Ic wylle swingan eow mid þam smeartestum swipum” (in Modern English, “I want to beat you with that smart whip”).
Although “smart” can still mean painful (“a smart slap in the face”), it’s used more often these days in the sense of intelligent, fashionable, neat, impertinent, or technically advanced (like a smart phone or a smart missile).
Some standard dictionaries describe the intelligent sense as chiefly American and the neat sense as chiefly British, though both usages can be heard on either side of the Atlantic.
Middle English writers widened the original painful sense of the adjective to include mental as well as physical pain.
In The Book of the Duchess (1369), for example, Chaucer writes: “Hym thought hys sorwes were so smerte” (“He thought his sorrows were so smart”).
Around the same time, the adjective took on a new sense—fast, rapid, brisk. Why? We haven’t seen an explanation, but it could be because the sting of a whip prompts a riding horse or a draft animal to speed up.
The earliest OED example of this speedy sense is from an English law, written sometime before 1325, that discusses novel disseisin, an old legal remedy to recover dispossessed lands:
“Þer nis no writ … ware-þoru þe plaintifs habbez smarttere riȝt þane þoru þe writ of nouele disseisine” (“There is no writ through which plaintiffs have faster justice than through the writ of novel disseisin”).
Later in the 1300s, the adjective “smart” came to mean lively, active, or prompt. And by the start of the 1400s, it meant forward, impudent, cheeky, or pert.
As you can see, the sense of being quick of foot was quickly evolving to mean quick of mind. By the 1570s, according to OED citations, the evolution was complete.
The dictionary’s first example of “smart” used to mean intelligent is from a 1571 poem by the Scottish ballad writer Robert Sempill: “Smart in my schuitting [shooting] & singular in my Science.”
This later example is from Argenis, a 1628 book by the Scottish satirist John Barclay: “For he, a smart young man, and of great iudgement … held vp the Kings side.”
In the early 1700s, the adjective took on the sense of neat and stylish. The OED’s first citation, referring to a stylish wig, is from The Lying Lover, a 1704 comedy by the Irish writer Richard Steele: “What shall I do for Powder for this smart Bob.”
In a few years, “smart” was being used in the sense of fashionable, elegant, and sophisticated. The first example in the OED is from a description of a painting in the March 27, 1719, issue of the Free-Thinker:
“In the rising Scale is a Cluster of smart Men, in tawdry Dresses, with little Rapiers, cocked Hats, and tied Wigs; holding divers Sorts of Mathematical instruments.”
In this better-known example, from Jane Austen’s novel Sense and Sensibility (1811), Edward Ferrars is speaking to Mrs. Dashwood:
“I always preferred the church as I still do. But that was not smart enough for my family. They recommended the army. That was a great deal too smart for me.”
So how did an adjective meaning painful and intelligent come to mean fashionable?
Our guess is that it might have evolved along the lines of “cute,” an abbreviated version of “acute” that progressed from clever, sharp, and shrewd to attractive, pretty, and charming.