nightcap n.

late Old English niht (West Saxon neaht, Anglian næht, neht) "the dark part of a day; the night as a unit of time; darkness," also "absence of spiritual illumination, moral darkness, ignorance," from Proto-Germanic *nahts (source also of Old Saxon and Old High German naht, Old Frisian and Dutch nacht, German Nacht, Old Norse natt, Gothic nahts).

The Germanic words are from PIE *nekwt- "night" (source also of Greek nyx "a night," Latin nox, Old Irish nochd, Sanskrit naktam "at night," Lithuanian naktis "night," Old Church Slavonic nosti, Russian noch', Welsh henoid "tonight"), according to Watkins, probably from a verbal root *neg- "to be dark, be night." For spelling with -gh- see fight.  The vowel indicates that the modern English word derives from oblique cases (genitive nihte, dative niht).

The fact that the Aryans have a common name for night, but not for day (q.v.), is due to the fact that they reckoned by nights. [Weekley]

Thus in Old English combinations night was "the night before (a certain day or feast day);" compare German Weihnachten "Christmas," literally "holy night." In early times, the day was held to begin at sunset, so Old English monanniht "Monday night" was the night before Monday, or what we would call Sunday night; so saeterniht "Friday night." The Greeks, by contrast, counted their days by mornings.

To work nights preserves the Old English genitive of time. Night soil "excrement" (1770) is so called because it was removed (from cesspools, etc.) after dark. Night train is attested from 1838; night-school from 1520s; night-life "habitual nocturnal carousing" is attested from 1852.

late Old English cæppe "hood, head-covering, cape," a general Germanic borrowing (compare Old Frisian and Middle Dutch kappe, Old High German chappa) from Late Latin cappa "a cape, hooded cloak" (source of Spanish capa, Old North French cape, French chape), a word of uncertain origin. Possibly a shortened from capitulare "headdress," from Latin caput "head" (from PIE root *kaput- "head").

The Late Latin word apparently originally meant "a woman's head-covering," but the sense was transferred to "hood of a cloak," then to "cloak" itself, though the various senses co-existed. Old English took in two forms of the Late Latin word, one meaning "head-covering," the other "ecclesiastical dress" (see cape (n.1)). In most Romance languages, a diminutive of Late Latin cappa has become the usual word for "head-covering" (such as French chapeau).

The meaning "soft, small, close-fitted head covering" in English is from early 13c., originally for women; extended to men late 14c.; extended to cap-like coverings on the ends of anything (as in hubcap) from mid-15c. The meaning "contraceptive device" is by 1916.

The meaning "cap-shaped piece of copper lined with gunpowder and used to ignite a firearm" is by 1825, hence cap-gun (1855); extended to paper strips used in toy pistols by 1872 (cap-pistol is from 1879).

Figurative thinking cap is from 1839 (considering cap is 1650s). Cap and bells (1781) was the insignia of a fool; cap and gown (1732) of a scholar. To set one's cap at or for (1773) means "use measures to gain the regard or affection of," usually in reference to a woman seeking a man's courtship.