The rule
I = 1 · V = 5 · X = 10 · L = 50 · C = 100 · D = 500 · M = 1000
Why it works
Roman numerals add symbol values from left to right, with one twist: a smaller symbol before a larger one is subtracted. That subtractive rule is what turns IIII into IV, and it is also where most mistakes come from.
How to do it by hand
- Take the largest symbol value that fits and write it
- Subtract it and repeat with what is left
- Use the subtractive pairs where they apply: IV, IX, XL, XC, CD, CM
- Reading back, subtract any symbol smaller than the one after it
What is worth knowing
The subtractive rule has strict limits that casual use ignores: only I, X and C may be subtracted, and only from the next two values up. So 99 is XCIX, not IC, even though IC looks reasonable. The system also has no zero and no way to write anything above 3999 without extra notation, which is exactly why it was abandoned for arithmetic. Clock faces are the famous exception to canonical spelling: many still use IIII rather than IV, a tradition with no agreed explanation but several competing stories.