The alt.usage.english FAQ   

• "dressed to the nines"

  (Phrase Origins)
  
  

  
     This expression, meaning "very fashionably and elaborately
  dressed", is recorded from the 18th century.  "The nine" or "the
  nines" were used to signify "superlative" in numerous other
  contexts.  Theories include:  9, being the highest single-digit
  number, symbolized the best; a metanalysis of Old English _to
  then eyne_ "to the eyes"; and a reference to the 9 muses.

  
  
  Source: [Mark Israel, 'Phrase Origins: "dressed to the nines"', The alt.usage.english FAQ file,(line 4679), (29 Sept 1997)]
  
  
  
  

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