Etymology
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homely (adj.)

late 14c., "of or belonging to home or household, domestic," from Middle English hom "home" (see home (n.)) + -ly (1). Sense of "plain, unadorned, simple" (as domestic scenes often were) is late 14c., and extension to "having a plain appearance, without particular beauty of features, crude" took place c. 1400, but survived chiefly in U.S., especially in New England, where it was the usual term for "physically unattractive;" ugly meaning typically "ill-tempered." In the old sense of "domestic, of or pertaining to domestic life," homish (1560s) and homelike (1789) have been used.

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homeliness (n.)

mid-14c., "meekness, gentleness," also "familiarity, intimacy; friendliness," from homely + -ness. Sense degenerated by c. 1400 to "want of refinement in manners, coarseness; presumptuousness." Meaning "lack of beauty" is by 1849.

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plain Jane 

"homely or unattractive woman, girl without beauty," attested by 1912, a rhyming formation from plain (adj.).

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homespun (adj.)

1590s, "spun at home," from home (n.) + spun. Figurative sense of "plain, homely" is from c. 1600. As a noun, "homemade cloth or clothing," from c. 1600.

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flog (v.)

1670s, slang, of uncertain origin. Perhaps a schoolboy shortening of Latin flagellare "flagellate" (see flagellum); Century Dictionary suggests perhaps from a Low German word "of homely use, of which the early traces have disappeared." OED finds it presumably onomatopoeic. Figurative use from 1800. Related: Flogged; flogging.

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chap-book (n.)

also chapbook, 1812, from chap, short for chapman, so called because chapmen once sold such books.

One of a class of tracts upon homely and miscellaneous subjects which at one time formed the chief popular literature of Great Britain and the American colonies. They consisted of lives of heroes, martyrs, and wonderful personages, stories of roguery and broad humor, of giants, ghosts, witches, and dreams, histories in verse, songs and ballads, theological tracts, etc. They emanated principally from the provincial press, and were hawked about the country by chapmen or peddlers. [Century Dictionary] 
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dowdy 

1580s (n.), "an aukward, ill-dressed, inelegant woman" [Johnson]; as an adjective, 1670s, "slovenly, shabby in dress" (of women). Perhaps a diminutive of Middle English doude "unattractive woman" (mid-14c.), which is of uncertain origin. Compare Scottish dow "to fade, wither, become dull or flat." In modern use it tends more toward "unfashionable, without style." 

If plaine or homely, wee saie she is a doudie or a slut [Barnabe Riche, "Riche his Farewell to Militarie profession," 1581]
You don't have to be dowdy to be a Christian. [Tammy Faye Bakker, Newsweek, June 8, 1987]

Modern use of dowdy (adj.) is likely a back-formation from the noun. Related: Dowdily; dowdiness.

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russet (n.)

mid-13c., "coarse, woolen cloth," usually of a subdued reddish-brown color; also (early 15c.) the color of this; from Old French rousset, from rosset (adj.) "reddish," diminutive of ros, rous "red," from Latin russus, which is related to ruber "red" (from PIE root *reudh- "red, ruddy").

As an adjective, "reddish," from late 14c. The name continued even when the cloth color was brown or gray. The coarse, homespun cloth also was indicative of rustic homely, simple persons or qualities (by 1580s). The adjective was applied to a type of apples by 1620s; as the name of a variety of eating apple by 1708; as a type of pear by 1725.

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blues (n.1)

"music form featuring flatted thirds and sevenths," possibly c. 1895 (though officially 1912, in W.C. Handy's "Memphis Blues"). Blue note "minor interval where a major would be expected" is attested from 1919, and at first was suspected as a source of the term. Also compare blues (n.2).

I am under the impression that these terms [blue note, blue chord] were contemporary with, if they did not precede and foreshadow, the period of our innumerable musical 'Blues.' What the uninitiated tried to define by that homely appellation was, perhaps, an indistinct association of the minor mode and dyspeptic intonation with poor digestion; in reality, it is the advent in popular music of something which the textbooks call ambiguous chords, altered notes, extraneous modulation, and deceptive cadence. [Carl Engel, "Jazz: A Musical Discussion," The Atlantic Monthly, August 1922]
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