In the early 1700s, you could do something — just about anything, apparently — “to the nines.” It would have sounded something like this citation from 1719: “How to the nines they did content me.” “To the nines” meant really good, to the highest point, nearing perfection. Unfortunately people’s ability to do most things that well seems to have eroded during the course of the 1700s until, by 1787 it was much more common to hear or read something more like “Last Saturday, one of those notorious villains, ?, dressed in his laced cloaths, and powdered off to the nines, went on board of a brig, bound for Calais.”
The earlier, generalized version of “to the nines” has pretty much disappeared by now, but it’s still possible to hear the phrase “dressed to the nines”. Nobody is quite sure where the phrase came from, but there are plenty of theories, and just about every book about word origins includes at least one of them. There is, to begin with, the sailing ship theory. This one points out that a three-masted sailing ship (which was a pretty common thing in the 1700s) would often have three spars on each mast. When you raised all the sails there were — nine, obviously — that would be in a sense sailing “at the highest rate,” or “to the nines.” Incidentally, a sidebar to this theory — which most word origin books also mention — is that the spars were also called “yards” and supposedly that gave rise to that other nine-ish expression “the whole nine yards.” This theory wraps everything up quite neatly, and as with many neat theories, there’s no evidence whatsoever to support it. As H.L. Menken (might have) said, “for every complex problem there is a solution that is simple, neat — and wrong.”
So if the sailing ship theory isn’t the one, you might want to go with the Army theory. This one suggests that in the British Army, the 99th Wiltshire Regiment was well known back in the day as a bunch of snappy dressers. Thus being “dressed to the nines” meant you were dressed just as well as those sartorially superior soldiers. This is also a neat and tidy theory, and also boasts zero evidence. There’s another item arguing against it, too: “to the nines” was originally used as a general term, not exclusively about clothes. All the stories about the 99th Regiment mention their outfits, but nobody ever said anything else about them was particularly impressive.
So on we go to the Old English theory. There was (or at least might have been) an Old English phrase “to then eyne”, which was supposed to have meant “pleasing to the eyes.” The pronunciation was garbled in the transition to Middle and Modern English, and became “to the nines.” The problem with this theory, of course, is that Old English is really old, and there’s no evidence of the phrase “to the nines” before the 1700s — and no evidence of the phrase “to then eyne” ever.
And finally we’re left with a messy and somewhat less than satisfying theory. These are characteristics that recommend it as the correct one. It is simply that, for no particular reason, the number 9 has always been a really popular number. Cats have nine lives, there were nine Muses in Greek mythology, and Hell is supposed to have nine levels (or circles, or whatever they are). The number nine appears in all sorts of stories and myths. So maybe doing something “to the nines” is no more than a convenient way to say “that’s really good.” But in our more advanced age, we’ve progressed. Reliable sources say that some rock bands have amplifiers that go all the way to eleven.
