The two different monogram types were made with different techniques. The most circle-ish one was made using cardboard print, the other was made using string print.
Cardboard print: That which is to be printed is first cut out from a sheet of cardboard using scissors or knife. Then it's glued to another sheet of cardboard and printed using spoon printing.
String print: That which is to be printed is shaped in a length of string that is glued onto a sheet of cardboard. After the glue is dry it is printed just like linoleum spoon printing.