Figurative meaning "a mark of disgrace" in English is from 1610s. Stigmas "marks resembling the wounds on the body of Christ, appearing supernaturally on the bodies of the devout" is from 1630s; earlier stigmate (late 14c.), from Latin stigmata.
"mixed-up, ridiculous, implausible," American English slang word attested by 1946, popularized c. 1960, but said to be New York City children's slang from mid-1920s; perhaps an alteration of decalcomania (see decal). There is a 1945 recorded use of the word apparently meaning a kind of temporary tattoo used by children.
mid-13c., peinten, "represent (someone or something) in paint;" c. 1300, "decorate (something or someone) with drawings or pictures;" early 14c., "put color or stain on the surface of; coat or cover with a color or colors;" from Old French peintier "to paint," from peint, past participle of peindre "to paint," from Latin pingere "to paint, represent in a picture, stain; embroider, tattoo," from a nasalized form of PIE root *peig- "to cut, mark by incision."
The sense evolution between PIE and Latin was, presumably, "decorate with cut marks" to "decorate" to "decorate with color." Compare Sanskrit pingah "reddish," pesalah "adorned, decorated, lovely;" Old Church Slavonic pegu "variegated;" Greek poikilos "variegated;" Old High German fehjan "to adorn;" Old Church Slavonic pisati, Lithuanian piešiu, piešti "to write." Probably also representing the "cutting" branch of the family is Old English feol (see file (n.2)).
From late 14c. as "represent persons and things in pictures or drawing, portray." To paint the town (red) "go on a boisterous or disorderly spree" is by 1884; to paint (someone or something) black "represent it as wicked or evil" is from 1590s. Adjective paint-by-numbers "simple" is attested by 1970; the art-for-beginners kits themselves date to c. 1953.