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Life is full of unsolvable mysteries. What wiped out the dinosaurs? Who was on the grassy knoll? Where do babies come from, and where do they go? Then there’s that most unsolvable mystery of all, which has plagued us at Van Winkle’s for at least the last week or so: Why are old-timey nightcaps so damn droopy?

First, a clarification of terms. The nightcap in question is the one commonly associated with the Victorian era — like the one Ebenezer Scrooge is shown wearing in the first edition of “A Christmas Carol” (1843) or in countless cartoons. It’s a model that fell out of fashion, like nightcaps themselves, with the advent of central heating: Long and pointy, often featuring a sort of ball — or pom-pom, if you will — at the top. But the ball is of less concern than the fundamental floppiness of the hat itself. Why so droopy? Is it form, function, or some nebulous marriage of the two?

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Historically speaking, nightcaps go way back. According to C. Willett Cunnington’s "The History of Underclothes," they were common garments as early as 1557, when English physician Andrew Borde wrote, “Let your nyght cap be of scarlet… to be made of a good thycke quylte of cotton, or els of pure flockes or of cleane wolle, and let the covering be of whyte fuystan.” 

Why so droopy? Is it form, function, or some nebulous marriage of the two?

Borde made no mention of the nightcap’s shape, though Cunnington suggests there may not have been a single dominant style. One of Borde’s contemporaries, William Vaughan, had rather different design principles: “Let your night cappe have a hole in the top,” he wrote, “through which the vapour may go out.” At the time, “vapors” were thought to be disease-causing mists that rose from the dirt; clearly a pom-pom would slow recovery.

The droopy — or, at least, pointy — nightcap appears to have entered the scene by the mid-17th century. In his 1651 memoirs, English nobleman Thomas Verney mentioned his possession of “thirty fine peaked night capps.” By 1771, according to Cunnington, nightcaps that were “baggy and had no tassel” were “the usual mode.”

They remained popular well into the next century. By 1849, “jellybag” nightcaps were “often coloured and generally tasseled,” worn mostly by men. Women wore a bonnet-like cap tied under the chin, which Cunnington ascribes to the “developing force of prudery” in the era. There is evidence that jellybag caps were fashionable more than functional: One writer noted that her husband occasionally switched out his baggy cap for a wool model buttoned under the chin, but this “was worn only for extra warmth; otherwise it was an unfashionable material.”

The droopy — or, at least, pointy — nightcap appears to have entered the scene by the mid-17th century.

This is a telling observation, given that most contemporary explanations follow the not-quite-logic that droopy caps provided extra warmth. Wikipedia, source of all sources, asserts, un-cited, that the length of the hat doubled as a scarf, keeping the neck warm as well as the head. Another source makes the unsubstantiated claim that they were “intended to trap warm air in a large exaggerated space.” This seems… thin, unless hats were made out of the same material as space blankets.

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Plus, droopy (daytime) hats were already part of the popular Western consciousness by the mid-1800s. The less-floppy-but-floppy-nonetheless Phrygian cap had been a symbol of liberty since the Roman republic, revitalized during the French Revolution. And Santa Claus started wearing his pointy, tasseled hat as early as the 1860s. In this light, the jellybag nightcap may simply have been the natural extension of contemporary fashion.

Until, of course, the younger generation stopped wearing them. Thanks to fashion-fickle Victorian youth, Cunnington writes, droopy nightcaps simply “did not survive” into the 1900s. Now they live only in old-timey pictures and cartoons, consigned to our collective nostalgia — for a time when life was simpler, hats were droopier, and disease rose from the ground in amorphous mists.