Dear Word Detective: I couldn’t find the phrase “dressed to the nines” in your archives. If it’s there, please point out the location to me. If not, will you discuss it, please? — Dick Stadler.
How strange. Seriously, this is weird. I knew for a fact that I had answered this question at least once in the past 16 years, but you’re right, the column is not in the archive index on my web site. Maybe the web moths ate it. In any case, I’ve written approximately 2,000 columns (no joke) since I last tackled “dressed to the nines,” so I guess it’s time for a rerun.
The earliest that “dressed to the nines” (or a closely related form), meaning “dressed very elaborately or fashionably,” has been found in print is the late 18th century (“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,”1787). The use of just “to the nines” in a more general sense to mean “to the highest point, to perfection” has been found about a half-century earlier (“How to the nines they did content me,” 1719). That more general sense is rarely heard today, but “dressed to the nines” is very much alive and well in the modern English vernacular (“If you’ve got money to splurge, then sure, be dressed to the nines in some designer label,” Malaysia Star, 12/07/10).
“Dressed to the nines” is also, and has been almost since its first appearance in print, one of the most popular objects of speculation among etymologists of varying competence. It’s rare to find a book or website devoted to word origins that doesn’t take a crack at the phrase. Unfortunately, many of these efforts wind up endorsing theories that, for one reason or another, are either probably not true or borderline nuts. One theory, for instance, traces the phrase to a three-masted sailing ship, each mast having three “yards,” or spars. Under full sail (i.e., “at the highest point”), that gives you nine sails. This theory also, as a questionable bonus, neatly ties “to the nines” to a popular story about the phrase “the whole nine yards” coming from the same arrangement of sails. Unfortunately, there is precisely zero evidence that either theory is true.
Another popular theory traces the phrase to the 99th Wiltshire Regiment of the British Army, supposedly known as snappy dressers in the 19th century. But, once again, a complete lack of actual evidence spoils the fun. Simply because a theory “makes sense” doesn’t mean it’s true. And, as a matter of fact, the 99th Regiment theory leapfrogs over the prior use of “to the nines” to mean “excellently” with no reference to sartorial splendor.
Yet another theory, of which I have always been fond (possibly in part because my parents tentatively endorsed it in their Morris Dictionary of Word and Phrase Origins), traces “to the nines” to a hypothetical Old English phrase “to then eyne,” meaning in modern English “to the eyes” or “pleasing to the eyes,” which was, goes the theory, later garbled into “to the nines.” The best you can say about this theory is that it is not absolutely slam-dunk impossible. It is, however, unlikely that sometime in the centuries between Old English and the early 1700s some form of “to the nines” wouldn’t have popped up in print.
The most likely explanation of “dressed to the nines” (and “to the nines” as a simple superlative) lies in the number nine itself, which has exerted a curious attraction on humanity pretty much since we learned to count. Classical mythology sported nine muses, cats have nine lives, and Hell has, it is said, nine levels (not counting Walmart). Hugh Rawson, in his fine book Devious Derivations (1994), notes that our long-standing affection for the number nine ranges from Scandinavian mythology, where there were nine earths (coinciding spookily with the nine planets in our solar system) to the very modern assertion that “possession is nine points of the law.” Nine is also three times three, a symmetry that has long figured in magic and numerology. And nine is, of course, the closest you can get to ten, the “highest setting” (for those of us not Nigel Tufnel, at least) in many contexts. So if someone says that you are “dressed to the nines,” you’ve flown as close to the white-hot pinnacle of fashion as it’s advisable to get.