At Sixes and Sevens: A state of total confusion and disorder. A person who is at sixes and sevens is in a quandary and doesn’t know quite what to do next.
The earliest use of the phrase is generally credited to be in Chaucer’s Troilus and Criseyde, 1374. “To set the world at six and seven” seems, in this context, to mean to hazard the world or to risk one’s life.
A fairly common theory is that the original form of the phrase was ‘to set on six and seven’, thought to have derived from a 14th century game of dice in which to try a throw of six and seven was a very risky gamble. Some claim the game was hazard, which had a set of rather arbitrary rules. ‘Six and seven’ is probably a corruption of ‘cinque and sice’, which is French for the numerals five and six. These were apparently the most dangerous numbers to set on, or roll, and anyone who tried for them was considered careless or confused.
Another theory, provided by phrases.org.uk, is that the saying originates from a situation relating to the Guilds of Tradesmen in the City of London in 1327. The Merchant Taylors and the Skinners were founded within a few days of each other, five other Guilds having already received their charters. The age of each Guild dictated its position in the Lord Mayor’s procession. The Merchant Taylors and the Skinners argued for fifty years as to which should go sixth in the procession. Eventually, a compromise was reached by which they agreed to exchange sixth and seventh place each year.
A third explanation, this one from theanswerbank.co.uk, is that the expression ‘set upon six and seven’, comes from the trade of needlemaking. When the needles are jumped up, they are said to be sixes and sevens because those numbers are the sizes most generally used, and in their manufacture they have to be frequently distinguished from each other. I have my doubts.
I also found reference to a similar phrase with a different meaning in the Bible (Job 5:19). ‘From six calamities he will rescue you; in seven no harm will befall you.’ Which doesn’t seem to have much to do with needles, guilds, or dice.
Other forms of the phrase are ‘set at six and seven’, ‘stand on six and seven’, and ‘to be left at six and seven.’ It wasn’t until the 18th century that the numbers became plural. According to the 1785 Dictionary of the Vulgar Tongue, ‘left at sixes and sevens’ means ‘in confusion, commonly said of a room where the furniture, etc., is scattered about, or of a business left unsettled.’
Oddly, Partridge’s Dictionary of Slang and Unconventional English doesn’t mention the phrase at all.
However, according to Mr. Partridge:
Six-and-eightpence is ‘The usual Fee given, to carry back the Body of the executed Malefactor, to give it a Christian burial’, late C.17-mid-18. Also a solicitor or attorney, 1756, because this was a usual fee.
Six-and-tips is whiskey and small beer, ca. 1780-1850.
A six-pounder was ‘A servant maid, from the wages formerly given to maid servants, which was commonly six pounds per annum, plus keep.’ Ca. 1780-1850.
And a donkey’s breakfast was a straw hat, ca. 1893.