In advance: Make cookies. Prepare and roll out dough. Use pattern to cut flags; use round cutter
to cut bases. Bake and cool cookies.
Also in advance: Iceflags. Use toothpick to mark 4 horizontal rows of 3/8 in. wide checks. Pipe tip 2 outlines using black full-strength icing; flow in alternating checks using thinned black and white icing. Let dry.
Finally in advance: Ice bases. Pipe tip 3 outlines using full-strength icing; flow in using thinned icing. Let dry.
Trim and assemble using full-strength icing and tip 3. Print name on flag. Pipe outline track details on base. Attach flag to base; position Topper.