1683, a name applied disparagingly by Dutch settlers in New Amsterdam (New York) to English colonists in neighboring Connecticut. It may be from Dutch Janke, literally "Little John," diminutive of common personal name Jan; or it may be from Jan Kes familiar form of "John Cornelius," or perhaps an alteration of Jan Kees, dialectal variant of Jan Kaas, literally "John Cheese," the generic nickname the Flemings used for Dutchmen.

[I]t is to be noted that it is common to name a droll fellow, regarded as typical of his country, after some favorite article of food, as E[nglish] Jack-pudding, G[erman] Hanswurst ("Jack Sausage"), F[rench] Jean Farine ("Jack Flour"). [Century Dictionary, 1902, entry for "macaroni"]

Originally it seems to have been applied insultingly to the Dutch, especially freebooters, before they turned around and slapped it on the English. A less-likely theory (attested by 1832) is that it represents some southern New England Algonquian language mangling of English. In English a term of contempt (1750s) before its use as a general term for "native of New England" (1765); during the American Revolution it became a disparaging British word for all American natives or inhabitants. Contrasted with southerner by 1828. Shortened form Yank in reference to "an American" first recorded 1778. Latin-American form Yanqui attested in English by 1914 (in Mexican Spanish by 1835).

The rule observed in this country is, that the man who receives that name [Yankee] must come from some part north of him who gives it. To compensate us for giving each other nicknames, John Bull "lumps us all together," and calls us all Yankees. ["Who is a Yankee?" Massachusetts Spy, June 6, 1827]

popular tune of the American Revolution, apparently written c. 1755 by British Army surgeon Dr. Richard Schuckburgh while campaigning with Amherst's force in upper New York during the French and Indian War. The original verses mocked the colonial troops (see Yankee) serving alongside the regulars, and the Doodle element might have been, or hinted at, the 18c. slang term for "penis." The song naturally was popular with British troops in the colonies during the Revolutionary War, but after the colonials began to win skirmishes with them in 1775, they took the tune as a patriotic prize and re-worked the lyrics. The current version seems to have been written in 1776 by Edward Bangs, a Harvard sophomore who also was a Minuteman.

abbreviated form of Yankee, 1778.

"inhabitant or native of the south," 1817, American English, from southern + -er (1). Contrasted with Yankee by 1828. Compare Southron. Souther "wind, gale, or storm from the south" is by 1851.

a vulgar drawling pronunciation of concerned, at first in England in representations of the speech of beggars, the Irish and sailors. The London Morning Chronicle, Sept. 28, 1829, has an account in which the speaker is imitating a sturdy beggar who describes himself as " 'consarned,' as he calls it, in liquor."

It appears in Yankee dialect humor pieces in U.S. newspapers by 1830 in "Letter from a Sailor in Paris" in the Albany Daily Advertiser, etc. (he was consarned about the Toolleries), but it might be meant as a sailor's word there, and the first record of it clearly representing simply Yankee pronunciation is 1834 in the Maj. Jack Downing letters. As an American English euphemism for "damned" it is attested by 1840.

by 1839, altered spelling of through; at first often in representations of dialect (Scottish, Yankee), by 1880s in standard use as a simplified spelling.

also darkey, darkie, colloquial for "a black person, a Negro" (now offensive), 1775, from dark (adj.) + -y (3). Related: Darkies.

Jake thought how strange it was to hear the Englishman say “darky” without being offended. Back home he would have been spoiling for a fight. There he would rather hear “nigger” than “darky,” for he knew that when a Yankee said “nigger” he meant hatred for Negroes, whereas when he said “darky” he meant friendly contempt. [Claude McKay, Home to Harlem, 1928.]

1520s, "brightness, radiance," from shine (v.). Indicating "sunshine," and paired with rain (n.), from 1620s. Meaning "polish given to a pair of boots" is from 1871.

For the American English slang meaning "a prank, a trick," see monkey-shines. Often also "a fancy, a liking," as in phrases such as take a shine to, "fancy," attested by 1830 in representations of Yankee dialect; shine up to "attempt to please as a suitor by making a brilliant impression" (1882).

The derogatory meaning "black person" is attested by 1908, perhaps from glossiness of skin or, on another guess, from frequent employment as shoeshines.

also sky-scraper, "very tall urban building," 1888, in a Chicago context, from sky (n.) + agent noun of scrape (v.). Used earlier for any thing which reaches or extends far up, such as "ornament atop a building" (1883), "very tall man" (1857), "high-flying bird" (1840), "light sail at the top of a mast" (1794), and the name of a racehorse (1789). Compare cognate French gratte-ciel, from gratter "to scrape" + ciel "sky;" German Wolkenkratzer, from Wolke "cloud" + Kratzer "scraper."

cloud-cleaver, an imaginary sail jokingly assumed to be carried by Yankee ships. [W. Clark Russell, "Sailors' Word Book," 1883]

"the southern United States," 1859, of obscure origin, first attested in the song of that name, which was popularized, if not written, by Ohio-born U.S. minstrel musician and songwriter Dan Emmett (1815-1904); perhaps a reference to the Mason-Dixon Line, but there are other well-publicized theories dating to the Civil War. Popularized nationwide in minstrel shows. Dixieland style of jazz developed in New Orleans c. 1910, so called by 1919 (in the name of a band).

It is interesting to remember that the song which is essentially Southern — "Dixie" — and that which is essentially Northern — "Yankee Doodle" — never really had any serious words to them. [The Bookman, June 1910]