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In a small bowl, combine confectioners’ sugar, vanilla and enough milk to make a thin icing consistency. Spread about 1 teaspoon icing over the top and sides of each cookie so that the texture of the cookie shows through.
To make gumdrop hats, roll a large gumdrop into an oval in granulated sugar. Roll oval into a cone shape; press to seal ends. Curl up bottom edge of cone to form a brim. Attach hat to head of peanut butter snowman with icing. Add candy decorations or decorator icing to make dots for eyes and buttons.