Interesting question - the numerals are basically additive with a need for a maximum of 3 equal symbols in a row. Above this you can have one subtractive symbol to the left of a larger symbol. (On some clocks this rule is violated with "IIX" for eight - this is incorrect and should be "VIII" always.) And then there is always another symbol for 5 times power of ten (V, L and D) until you get to thousands, for which you must keep going with as many "M"s as required.
Something like 1888 is 'orrible... = "MDCCCLXXXVIII"
There also seems to be a rule that the subtractive symbol must be only 1 power of ten less than its larger symbol to the right, but I can't find this rule written down.
e.g. 99 would be very convenient as "IC", but it actually is "XCIX", or 95 - not "VC" but "XCV".
Trivia: All possible symbols are "MDCLXVI" = 1666.