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foolscap (noun):

1: a cap or hood usually with bells worn by jesters
2: a conical cap for slow or lazy students
3 [from the watermark of a foolscap formerly applied to such paper] : a size of paper formerly standard in Great Britain

Source : Merriam -Webster

Etymology : You’d be well within your rights to respond “Surely, you jest!” to the notion that foolscap refers to a sheet of writing paper, and also specifically to a paper size of approximately 8″ x 13″, similar to that of a legal pad. After all, when foolscap was first used in the 1500s, it referred to an actual fool’s cap—the oft jingling headwear worn as part of a jester’s motley (a sense still used today). But we promise we do not jest. The connection between the whimsical chapeau and the paper is attributable to the former use of a watermark depicting a fool’s cap that was used on long sheets of writing or printing paper. There are various explanations for the introduction of this watermark—including the claim that a 1648 British parliamentary group substituted it for the royal arms during exceptionally turbulent times—but such explanations remain unsupported by historical evidence.

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