Q From Neil Paknadel; a related question came from Carol Nichols: Your questioner about crackerjack some time ago used squared away. Now we need an article on its figurative meaning, though I believe its origin is nautical.
A It is indeed a term from the days of sailing ships, though it has come ashore in its current figurative sense of being tidy or in proper order. It’s common in the armed forces, more so in the US than the UK.
Perhaps his first inspiration to serve was when his uncle, looking sharp and squared away in his military uniform, returned home from the Korean War and introduced himself to Lloyd when he was a little boy.
The Buffalo News (Buffalo, NY); 25 Nov. 2013.
We have numerous idioms employing square which imply related ideas of something that’s proper, correct, fair, honest, straightforward, precise or exact, all of which take us back to well-built structures whose corners are true right angles. Many are recorded for the first time in the sixteenth century and it was in that century, too, that we start to see examples of seafarers using square in various expressions, including square the yards.
It meant that the yards, the spars that carried the sails, were to be set at right angles to the keel line from bow to stern, a state that was known as square by the braces, or square by the lifts and braces if the spars were also set horizontal. (The lifts and braces were part of the running rigging; the lifts raised and lowered the yards and the braces turned them.) At sea, squaring the yards meant that the ship sailed directly downwind. After anchoring, square the yards was an instruction to clear the decks and make the ship tidy and ready for sailing again.
Near the end of the eighteenth century, sailors began to extend the verb by adding away. The combination took on a sense of getting moving or travelling directly to some destination without delay or deviation. This is the earliest I can find:
We have not anchored and shall not, as we shall square away for Canton in the evening.
From the entry of 30 August 1798 in the diary of Ebenezer Townsend, owner and supercargo of the Neptune. Reprinted by the Hawaiian Historical Society in 1888.
In the 1860s we begin to see square away being used by non-sailors in a way that approximates to our current sense and which developed from the sailing one — to make everything ship-shape or to get ready for some action. An early appearance:
I didn’t waste any time in sociabilities with Clarence, but squared away for business, straight-off.
A Connecticut Yankee in King Arthur’s Court, by Mark Twain, 1889.
Incidentally, from about 1820 in Britain, square away took on a distinct sense of putting oneself in a posture of defence ready for a fist fight, presumably by adopting the conventional pugilistic position with fists clenched and raised. (The American square off appeared about the same time; more recently, square up has been usual in Britain.) This usage of square away lies to one side of our modern meaning but presumably derives from the same source.