Pylimitics

One thing immediately evident to most visual observers of art, buildings, sculptures — almost anything — is balance; symmetry of composition or construction. If something is too “lopsided,” even if they can’t put their finger on exactly why, many people feel slightly uncomfortable. 

What they’re probably even more uncomfortable with is wondering about the origin of the word “lopsided.” It’s obviously a compound word made up of lop and side. The “side” part is also pretty obvious, but as for lop, there are four different verbs and eight different nouns in English. Anyway, as you probably know, “lopsided” means that two sides of something don’t match; one side might be larger, heavier, saggier, or less balanced than the other. That’s pretty much what it meant when Charles Dickens used it in 1842:

“An odd, lop-sided, one-eyed kind of wooden building.”

That’s close to the very original meaning, when “lopsided” (spelled “lapsided” at the time) first appeared in the early 1700s. At first it referred only to ships. “You will certainly have the Misfortune of a lapsided Ship,” reads one citation from 1711, and even today if your ship is unbalanced from one side to the other it’s not good. 

But back to all the lops. Tracking down which “lop” is “sided” starts out pretty easily. “Lop” at one time meant “spider,” but that’s clearly not it. In fact it doesn’t seem to be any of the 8 different nouns. The best candidates are a couple of verbs. The oldest verb version of “lop” initially meant trimming branches from a tree. It now means cutting off pretty much anything. So you probably could produce something lopsided by clumsy lopping. A better “lop” is the one that appeared in the late 1500s and meant “hanging loosely” or “drooping.” This is the “lop” you find associated with “lop-eared,” such as a “lop-eared rabbit.” It’s also (probably) the best fit as the “lop” that’s “sided.” 

On the other hand, though, it’s possible that the original spelling “lapsided” is a better clue, and we should be looking at “lap.” It’s not the “lap” you get when you sit down, but the other one, which at first meant a fold of cloth (such as something you wear). It became the basis of “overlap.” Too much overlap on one side (originally of a ship, remember) might also be behind the origin of “lopsided.” 

But there isn’t a lot of evidence for any of these origins — that is, the possible explanations aren’t lopsided in any direction.