Entries linking to uncool
prefix of negation, Old English un-, from Proto-Germanic *un- (source also of Old Saxon, Old Frisian, Old High German, German un-, Gothic un-, Dutch on-), from PIE *n- (source of Sanskrit a-, an- "not," Greek a-, an-, Old Irish an-, Latin in-), combining form of PIE root *ne- "not." Often euphemistic (such as untruth for "lie").
The most prolific of English prefixes, freely and widely used in Old English, where it forms more than 1,000 compounds. It underwent a mass extinction in early Middle English, but emerged with renewed vigor 16c. to form compounds with native and imported words. It disputes with Latin-derived cognate in- (1) the right to form the negation of certain words (indigestable/undigestable, etc.), and though both might be deployed in cooperation to indicate shades of meaning (unfamous/infamous), typically they are not.
It also makes words from phrases (such as uncalled-for, c. 1600; undreamed-of, 1630s; uncome-at-able, 1690s; unputdownable, 1947, of a book; un-in-one-breath-utterable, Ben Jonson; etc., but the habit is not restricted to un-; such as put-up-able-with, 1812). As a prefix in telegramese to replace not and save the cost of a word, it is attested by 1936.
Old English col "not warm" (but usually not as severe as cold), "moderately cold, neither warm nor very cold," also, figuratively, of persons, "unperturbed, undemonstrative, not excited or heated by passions," from Proto-Germanic *koluz (source also of Middle Dutch coel, Dutch koel, Old High German chuoli, German kühl "cool," Old Norse kala "be cold"), from PIE root *gel- "cold; to freeze."
Attested in a figurative sense from early 14c. as "manifesting coldness, apathy, or dislike." Applied since 1728 to large sums of money to give emphasis to amount. Meaning "calmly audacious" is from 1825.
Slang use of cool for "fashionable" is by 1933, originally African-American vernacular; its modern use as a general term of approval is from the late 1940s, probably via bop talk and originally in reference to a style of jazz; the word is said to have been popularized in jazz circles by tenor saxophonist Lester Young (1909-1959). Cool-headed "not easily excited or confused" is from 1742.