"Dressed to the nines"
Yesterday, I wondered aloud whence came the phrase dressed to the nines. "Go look it up," my friends told me, although I was already halfway to my bookshelf. Surprisingly, my Facts on File: Encyclopedia of Word & Phrase Origins tome contained nothing on the phrase.
The Word Detective, one of my favorite websites, had this to say:
Dear Evan: Recently, I have begun to question my own dearly-held cliches. The most baffling is "dressed to the nines." Nine what? And how far does one need to dress to get there? Can one in fact dress only to the eights or less? Please don't laugh -- I'm semi-serious. -- Bill Thorn, via the Internet.
Well, if your question is semi-serious, you've come to the right place, because I have quite a few semi-serious answers for you. Incidentally, I rarely laugh at readers' questions. For one thing, it's your job to laugh at my answers, and, for another, most of my readers are big, burly guys who don't cotton to being mocked. That's what my editor tells me, anyway.
There are, as I've implied, a whole slew of possible origins of "dressed to the nines," meaning to be dressed in an elegant or elaborate fashion. One theory is that it came from an Old English saying "dressed to the eyes," or to please the beholder, which, in the peculiar spelling of Old English, would have appeared "dressed to then eyne." Through a process called "metanalysis," in which letters from one word migrate over time to a neighboring word, "then eyne" might have become "the neyne" and then "the nines." A similar metanalytic process transformed "a napron" (related to "napkin") to our modern "an apron."
On the other hand, the number nine holds an exalted place in numerology, and might have been adopted in the distant past as a synonym for "superlative." "Dressed to the nines" would thus be equivalent to our modern "dressed to the max."
It's also possible that the phrase come from an old jeweler's phrase "nine nines fine," referring to gold of 99.9999999 percent purity, or that the phrase refers to the nine muses of classical mythology, or to the spiffy uniforms of the 99th Wiltshire Regiment in England, or, well, you get the idea. There is no one answer, so I guess you'll just have to pick the theory you like best. Personally, I like the one about 99 bottles of beer.
The OED did not have any etymological info, but it did mention that "to the nines" wasn't a measurement used solely for dressing up:
(up) to the nines (rarely nine): to perfection, to the highest degree or point. In later use chiefly in dressed (up) to the nines: dressed very elaborately or smartly.
1719 W. HAMILTON Epist. to Ramsay 24 July in Familiar Epist. 8 How to the nines they did content me. 1787 ndependent Gazetteer (Philadelphia) 24 Mar. 2/3 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. a1796 R. BURNS Poems & Songs (1968) I. 327 'Twad please me to the Nine. a1796 R. BURNS Poems & Songs (1968) I. 192 Thou paints auld nature to the nines. 1821 J. GALT Ayrshire Legatees viii. 218 He's such a funny man! and touches off the Londoners to the nines. 1837 Herald (N.Y.) 11 Mar. 2/4 One evening a smart young mechanic, ‘dressed to the nines’, as Ben Bowline says, might have been seen wending his way along Broadway. 1863 C. READE Hard Cash I. 203 Being clad in snowy cotton and japanned to the nine. 1876 T. HARDY Hand of Ethelberta I. i. 4 When she's dressed up to the nines for some grand party. 1928 J. GALSWORTHY Swan Song I. viii. 63 Women then were defended up to the nines. 1963 N. C. E. KENRICK Story Wiltshire Regim. ix. 86 The 99th's sartorial perfection at this time [c1850] is said to have given rise to the expression ‘Dressed up to the nines’ as the other Regiments in Aldershot were constantly trying to achieve the same standard. 1979 J. COOPER Class (1980) ix. 208 He will decorate it to the nines to impress other rising pop stars. 2001 Courier (Dundee) Dressed to the nines in a morning suit and top hat, he was hired by the tourist office to distribute leaflets.