"Dressed to the nines Meaning Dressed flamboyantly or smartly. Origin The phrases 'to the nines', or 'to the nine', were used to indicate perfection - the highest standards. That was in use in the 18th century, as here from William Hamilton's Epistle to Ramsay, 1719: "How to the nines they did content me." 'To the nine' also appears in a translation of Voyages de Jehan de Mandeville chevalier, which appeared anonymously in France, circa 1357 and is attributed to Sir John Mandeville: "Sir king! ye shall have war without peace, and always to the nine degree, ye shall be in subjection of your enemies, and ye shall be needy of all goods." The original work was written in Anglo-Norman French and is much translated. Whether the 'to the nine' is a literal translation from the original or whether it was added by translators later, and possibly as late as 1900, isn't clear. It doesn't seem likely that the phrase existed in English as early as the 14th century, not to appear again in print until the 18th century. 'To the nines' has now gone out of use and only persists in the more specific 'dressed to the nines' (or sometimes 'dressed up to the nines'). Dressed to the nines, or dressed up to the nines are merely a version of the phrase that is applied to clothing. That is first cited in John C. Hotten's A Dictionary of Modern Slang, Cant, and Vulgar Words, 1859 as: "DRESSED UP TO THE NINES', in a showy 'recherché' manner." Many theories abound as to what prompted the phrase to be used in reference to dress. The fact that the prior phrase to the nines had been in existence for at least 150 years before we see dressed to the nines makes it obvious that the derivation of the variant version of the phrase need have had no connection with the number nine. Despite this, various attempts have been made to guess at the origin. One has it that tailors used nine yards of material to make a suit (or according to some authors a shirt). The more material you had the more status, although nine yards seems generous even for a fop. Another commonly repeated explanation comes from the reportedly smart uniforms of the The Wiltshire Regiment (Duke of Edinburgh’s) 99th Foot, which was raised in 1824. The problem with these explanations is that they come with zero hard evidence to support them, apart from a reference to the number nine (or even 99, which seems to be stretching the cloth rather thinly). The regiment was raised in the early 19th century, which is the right sort of date for the phrase to begin to be used in the middle of that century. It is at least plausible that the to the nines phrase was matched with the 99 of the regiment's name to and reputation to coin dressed to the nines. As we have seen ad nauseam with similar attempts to explain the whole nine yards, there are many things that come in groups of nine. Almost anything associated with the number has been at some point put forward as the origin of this phrase. The fact is, we aren't sure. While no one knows the origin of 'to the nines' it is worth noting that nine has been used as a superlative in other contexts. Classical mythology gave us the nine Muses of arts and learning. The Nine Worthies were drawn from the mythology, history and the Bible. This distinguished group was Joshua, David, Judas Maccabæus, Hector, Alexander, Julius Cæsar, Arthur, Charlemagne, and Godfrey of Bouillon. We also have the nine days' wonder. All of the above would have been well-known when this phrase was coined. A more recent link between nine and excellence is 'cloud nine'. " Source: http://www.phrases.org.uk/meanings/dressed-to-the-nines.html

Normally, the officers kept some of the allotment for themselves, but the Ninth's allotment being completely spent on uniforms made them the best dressed regiment in the British army. According to Michael Quinion in his book Port Out, Starboard Home: The big problem with this explanation is that the phrase to the nines is actually a good deal older ? it was first recorded in the late 18th century in poems by Robert Burns. In its earlier days it wasn't linked to high standards of dress but to any superlative situation: people could refer to "praising a man's farm to the nines", for example. http://www.mootgame.com/ballast/N1329A.html Common lore has it that a tailor making a high quality suit uses more fabric. The best suits are made from nine yards of fabric. This may seem like a lot but a proper suit does indeed take nine yards of fabric. This is because a good suit has all the fabric cut in the same direction with the warp, or long strands of thread, parallel with the vertical line of the suit. This causes a great amount of waste in suit making, but if you want to go "dressed to the nines", you must pay for such waste. New years eve is the one day of the year when people like to go out dressed to the nines. http://www.pride-unlimited.com/probono/idioms1.html Dress to kill is also used in the same sense. http://www.englishclub.com/vocabulary/idioms-clothing.htm This saying originated in Shakespeare's time and is connected with the price a person had to pay for theater tickets depending on where their seats were located. The farthest seats were one pence and the ones closest to the stage were nine pence. If you sat in the expensive seats you would feel obliged to dress up so as not to look out of place with the other wealthy patrons. http://members.aol.com/MorelandC/HaveOrigins.htm This expression is, according to the complete Oxford English Dictionary, recorded from 1793 in the poetry of Robert Burns: 'Thou paints auld Nature to the nines', it is recorded in a slang dictionary published in 1859. Slang is always difficult to pin down, and old slang is almost impossible. There are many expressions connected with the number nine, including 'nine days' wonder'. http://www.askoxford.com/asktheexperts/faq/aboutwordorigins/nines?view=uk