Etymology From Middle English up sid doun, an alteration of earlier upsadowne, upsedowne, up-so-doun (“upside down”), equivalent to up + so + down, literally “up as down”.
1
Inverted, so that the top is now at the bottom.
The Union flag was flying upside down, a sign of danger.
His hands were busy with his garments all this time: turning them inside out, putting them on upside down, tearing them, mislaying them, making them parties to every kind of extravagance.1843 December 19, Charles Dickens, “Stave Five. The End of It.”, in A Christmas Carol. […], London: Chapman & Hall, […], →OCLC, page 153:
1 more example
For, suddenly, I saw you there / And through foggy London town / The sun was shining upside down!1937, “A Foggy Day (In London Town)”, Ira Gershwin (lyrics), George Gershwin (music):
2
In great disorder.
The thief had turned the room upside down.
Peaſe and beanes are as danke here as a dog and that is the next way to giue poore iades the bots: this houſe is turned vpſide downe ſince Robin Oſtler died.c. 1597 (date written), [William Shakespeare], The History of Henrie the Fourth; […], quarto edition, London: […] P[eter] S[hort] for Andrew Wise, […], published 1598, →OCLC, [Act II, scene i], signature C2, recto:
Etymology From Middle English up sid doun, an alteration of earlier upsadowne, upsedowne, up-so-doun (“upside down”), equivalent to up + so + down, literally “up as down”.
1
Inverted; turned so that the top is at the bottom.
The pattern resembled an upside down letter W.
2
In great disorder.
The wenches and the men have been on the streets all day, and the kitchen is upside down. You never saw the like.1901, Amelia Edith Huddleston Barr, The lion's whelp: a story of Cromwell's time, page 248:
3
Business, Finance Owing more money for something than it is worth; having negative equity.