Step 1: Preheat oven to 325 degrees F.
Step 2: In a large mixing bowl beat butter with an electric mixer on medium to high speed for 30 seconds.
Step 3: Add sugar. Beat until combined, scraping bowl occasionally.
Step 4: Beat in milk and vanilla until combined.
Step 5: Beat in as much of the flour as you can with the mixer. Stir in any remaining flour.
Step 6: Remove 1 cup of the dough. Tint the remaining dough with red food coloring.
Step 7: For each cookie, shape red dough into one 1-inch ball and five 1/2-inch balls.
Step 8: Shape plain dough into one 3/4-inch ball and four 1/4-inch balls.
Step 9: Place the red 1-inch ball on an ungreased cookie sheet; flatten until 1/2 inch thick. Attach the plain 3/4-inch ball for head; flatten until 1/2 inch thick. Attach four of the red 1/2-inch balls for arms and legs; attach the plain 1/4-inch balls for hands and feet. Shape and attach the remaining red 1/2-inch ball for a hat.
Step 10: Repeat with remaining dough, placing cookies 2 inches apart. Add chocolate pieces for eyes and buttons.
Step 11: Bake for 12 to 15 minutes or until edges are lightly browned. Cool on cookie sheet for 2 minutes. Carefully transfer to a wire rack; cool.
Step 12: Icing: In a small mixing bowl beat shortening and vanilla with an electric mixer on medium speed for 30 seconds. Gradually beat in 1-1/3 cups of the powdered sugar until smooth. Beat in 1 tablespoon of the milk. Gradually beat in the remaining powdered sugar and enough milk to make frosting a piping consistency.
Step 13: Use frosting for beards and trip on hats. Attach cinnamon candies with small dabs of frosting for noses. Let stand until frosting is set.
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