In advance: Make cookies. Roll out dough and cut using largest boy cutter from set. Bake and cool.
Also: Make cakes. Fill pumpkin cavities 1/2 full; bake and cool cakes. Unmold; trim off facial features with knife. Cover pumpkins with heated decorator icing. Let set.
Set cookies on waxed paper; decorate using full-strength royal icing. Attach cake head to cookie with icing. Build up top of hat with tip 10 (smooth with finger dipped in cornstarch).
Pipe tip 104 ruffle hat brim. Pipe tip 44 (smooth side up) stripe hat band. Add details with tip 3. Outline and fill in shirt, pants and shoes; smooth. Outline and fill in pocket; add dot buttons (flatten with finger dipped in cornstarch). Pipe pull-out hay.
Outline and fill in eyes and nose; smooth. Pipe tip 2 outline mouth; add dot pupils (flatten slightly) and nose details. Pipe tip 103 ruffle collar; add tip 3 dot cheeks (flatten and smooth with finger dipped in cornstarch).