This article is from the alt.usage.english FAQ, by Mark Israel misrael@scripps.edu with numerous contributions by others.
It is sometimes said that the dollar sign's origin is a narrow
"U" superimposed over a wide "S", "U.S." being short for "United
States." This is wrong, and the correct explanation also tells why
the $ sign is used both for dollars and for pesos in various
countries. The explanation is not widely known, maybe because not
many people would think to look for it in a book called "A History
of Mathematical Notations, Volume II: Notations Mainly in Higher
Mathematics" by Florian Cajori (published in 1929 and reprinted in
1952, by Open Court Press). Cajori acknowledges the "U.S." theory
and a number of others, but, after examining many 18th-century
manuscripts, finds that there is simply no evidence to support those
theories.
Spanish pesos were also called piastres, Spanish dollars, and
pieces of eight. (The piece of eight was so called because its
value was eight reales. Some countries made one-real coins by
slicing pieces of eight into eight sectors; the still-current U.S.
slang "two bits" for a quarter of a dollar may refer to this,
although "bit" denoting any small coin -- as in "threepenny bit" --
was already in use.) The coins were circulated in many parts of the
world, much as U.S. dollars are today. The coins were so well known
that, when the U.S. got around to issuing its own silver coinage
(U.S. dollar coins first appeared in 1794), it simply replicated the
Spanish unit's weight and hence value, and even one of its names; so
it was natural to use the same symbol.
Since three of the four names given above for the Spanish dollar
start with p (and pluralize with s), it was natural for
abbreviations like p and ps to be used. Sometimes ps was written as
s P
 
Continue to: