inside-out (adj.)

late 14c., ynneside "interior part (of the body)," compound of in (prep.) + side (n.). General sense "inner side or part (of anything)" is from c. 1500.

The adjective sense "being on the inside" is from 1610s, from the noun. It began to be used in slang c. 1900 in reference to the supposed real facts or situation that only an insider would know. Inside man is from 1911 (originally in reference to workers used by management to sniff out union activity); inside job "robbery, espionage, etc., committed by or with the help of a resident or servant of a place" is attested by 1887, American English (also, late 19c., early 20c., "indoors work").

The figurative inside track "advantage" (1854) however is a metaphor from horse racing (1830); inside lanes are shorter than the outer ones on a curved track. Adverbial use in American English inside of (in reference to time) is from 1839.

expressing motion or direction from within or from a central point, also removal from proper place or position, Old English ut "out, without, outside," from Proto-Germanic *ūt- (Old Norse, Old Frisian, Old Saxon, Gothic ut, Middle Dutch uut, Dutch uit, Old High German uz, German aus), from PIE root *uidh- "up, out, up away, on high" (source also of Sanskrit ut "up, out," uttarah "higher, upper, later, northern;" Avestan uz- "up, out," Old Irish ud- "out," Latin usque "all the way to, continuously, without interruption," Greek hysteros "the latter," Russian vy- "out").

Sense of "to a full end, completely, to a conclusion or finish" is from c. 1300. Meaning "so as to be no longer burning or alight; into darkness" is from c. 1400. Of position or situation, "beyond the bounds of, not within," early 15c. Meaning "into public notice" is from 1540s; that of "away from one's place of residence," c. 1600. The political sense of "not in office, removed or ejected from a position" is from c. 1600. Meaning "come into sight, become visible" (of stars, etc.) is by 1610s. In radio communication, a word indicating that the speaker has finished speaking, by 1950.

As a preposition, "out of; from, away from; outside of, beyond; except; without, lacking;" mid-13c., from the adverb.

Meaning "from harmonious relations, into quarreling" (as in to fall out) is from 1520s. Meaning "from one's normal state of mind" (as in put out) is from 1580s; out to lunch "insane" is student slang from 1955. Adjectival phrase out-of-the-way "remote, secluded" is attested from late 15c. Out-of-towner "one not from a certain place" is from 1911. Out of this world "excellent" is from 1938; out of sight "excellent, superior" is from 1891. To (verb) it out "bring to a finish" is from 1580s. Expression from here on out "henceforward" is by 1942. Out upon, expressing abhorrence or reproach, is from early 15c.