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This article is from the alt.usage.english FAQ, by Mark Israel misrael@scripps.edu with numerous contributions by others.

140 "dressed to the nines" (Phrase origins - alt.usage.english)

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.

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