Bake and cool cookies made with medium round Cut Out for head. Use tip 3 and white royal icing to outline and pipe-in head (smooth with finger dipped in cornstarch); let dry.
To make hat, cut 1/4 in. off bottom of jumbo black spice drop; top will be used for top of hat. Roll out cut off piece of jumbo black spice drop flat on surface sprinkled with granulated sugar. Use medium Cut-Out to cut brim. Attach top of hat to brim with royal icing.
Use tip 3 and black royal icing to pipe dot eyes and outline mouth.
Use tip 4 and orange royal icing to pipe pull-out nose; let dry.
Cut lollipop stick to 3 in. length and attach to back of cookie with melted candy; let set.
Use tip 12 and white buttercream icing to build up round shape on cupcake; ice smooth with spatula and pat with finger dipped in cornstarch.
Position head on cupcake. Roll out jumbo red spice drop on surface sprinkled with granulated sugar and cut 3/8 in. wide piece for scarf. Wrap scarf around neck. Use tip 3 and black buttercream icing to pipe buttons.