When you hear the word foolscap, maybe the image that pops into mind is an old-time schoolhouse with an unruly student seated in the corner wearing the pointed cap of shame. That kind of cone-shaped hat did exist, but it was called a dunce cap. A fool, on the other hand, was what we would now think of as a court jester, and their associated hat was of the variety that would curl up and out into several points, perhaps with a jingling bell attached to the tip of each. The fool and his coxcomb were such an iconic image that, starting as early as the 1500s, they were even used as the watermark to indicate a particular size of paper. So while fool’s cap is worn by a fool, foolscap—as a single world—is a size of paper, and is unlikely to be worn by anyone.
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