Old English werian "to clothe, put on, cover up," from Proto-Germanic *wasīn- (source also of Old Norse verja, Old High German werian, Gothic gawasjan "to clothe"), from PIE *wos-eyo-, suffixed form of *wes- (2) "to clothe," extended form of root *eu- "to dress."
The Germanic forms "were homonyms of the vb. for 'prevent, ward off, protect' (Goth. warjan, O.E. werian, etc.), and this was prob. a factor in their early displacement in most of the Gmc. languages" [Buck]. It shifted from a weak verb (past tense and past participle wered) to a strong one (past tense wore, past participle worn) in 14c. on analogy of rhyming strong verbs such as bear and tear. Secondary sense of "use up, gradually damage" (late 13c.) is from effect of continued use on clothes. To wear down (transitive) "overcome by steady force" is from 1843. To wear off "diminish by attrition or use" is from 1690s.
Especially "opportunity afforded by freedom from necessary occupations" (late 14c.). "In Fr. the word has undergone much the same development of sense as in Eng." [OED]. The -u- appeared 16c., probably on analogy of pleasure (n.), etc. To do something at leisure "without haste, with deliberation" (late 14c.) preserves the older sense. To do something at (one's) leisure "when one has time" is from mid-15c.
1794, "unfruitful, futile," from Latin otiosus "having leisure or ease, unoccupied, idle, not busy" (source of French oiseux, Spanish ocioso, Italian otioso), from otium "leisure, free time, freedom from business," a word of unknown origin. Meaning "at leisure, idle" is recorded from 1850. Compare Latin phrase otium cum dignitate "leisure with dignity." Earlier adjective in English was otious "at ease" (1610s), and Middle English had noun otiosity (late 15c.).
c. 1200, from Old English æmettig, of persons, "at leisure, not occupied; unmarried" (senses now obsolete), also, of receptacles, "containing nothing," of places, "unoccupied," from æmetta "leisure."
Watkins explains it as from Proto-Germanic *e-mot-ja-, with a prefix of uncertain meaning + Germanic *mot- "ability, leisure," possibly from PIE root *med- "take appropriate measures." A sense evolution from "at leisure" to "containing nothing, unoccupied" is found in several languages, such as Modern Greek adeios "empty," originally "freedom from fear," from deios "fear." "The adj. adeios must have been applied first to persons who enjoyed freedom from duties, leisure, and so were unoccupied, whence it was extended to objects that were unoccupied" [Buck].
The -p- is a euphonic insertion. Of words, etc., "destitute of force or effect," mid-14c. Related: Emptier. The figurative sense of empty-nester is attested by 1960.
late 14c., "freedom from obligations, leisure, release" (from some activity or occupation), from Old French vacacion "vacancy, vacant position" (14c.) and directly from Latin vacationem (nominative vacatio) "leisure, freedom, exemption, a being free from duty, immunity earned by service," noun of state from past-participle stem of vacare "be empty, free, or at leisure," from PIE *wak-, extended form of root *eue- "to leave, abandon, give out."
Meanings "state of being unoccupied," "process of vacating" in English are early 15c. Meaning "formal suspension of activity, time in which there is an intermission of usual employment" (in reference to schools, courts, etc.) is recorded from mid-15c. As the U.S. equivalent of what in Britain is called a holiday, it is attested from 1878.