Roll out cookie dough and use medium round Cut-Out to cut Santa's head. Bake and cool. Use tip 3 and copper royal icing to outline and pipe in face (smooth with finger dipped in cornstarch). Roll out jumbo green spice drop on surface dusted with granulated sugar and cut elf's hat shape. Attach hat to head with buttercream icing. Position head on waxed paper and use tip 3 and white royal icing pipe pull-out fringe on hatband and pom pom. Use tip 3 and black royal icing to pipe eyes and mouth. Use tip 3 and copper royal icing to pipe dot nose. Pipe tip 5 copper royal icing pull-out ears. Pipe tip 3 rose royal icing cheeks (smooth with finger dipped in cornstarch). Let dry.
Bake and cool cupcakes. Use tip 12 and red buttercream icing to pipe mound of icing on cupcake, ice with spatula and smooth with finger dipped in cornstarch. Use tip 12 and red buttercream icing to pipe arms. Pipe tip 3 hands with copper royal icing. Pipe tip 3 green buttercream ribbon and bow on sugar cube and position in hands. Use tip 3 and white royal icing to pipe dot buttons and fur around cuffs.