Beat butter with an electric mixer on medium to high speed for 30 seconds. Add granulated sugar, vanilla, and 1/4 teaspoon salt; beat until combined. Beat in as much of the flour as you can with mixer. Stir in any remaining flour with a wooden spoon.
For each snowman you,ll need to shape 3 balls of the dough ^ one 1-inch ball, one 3/4-inch ball, and one 1/2-inch ball. Roll a portion of the dough between both hands ^ this is a job that the kids can do. Use a ruler to measure the size of dough balls.
Place 3 balls for each snowman, on cookie sheet, in decreasing sizes with the edges just touching. Press the balls together slightly but not enough that you change the shape of the balls. Leave about 1-1/2 inches of space between each snowman cookie.
Insert 2 miniature semisweet chocolate pieces in the smallest ball for the eyes, 1 chocolate piece in the middle ball for a button, and 2 chocolate pieces in the largest ball for two more buttons. Line up the buttons in the medium and large balls. Bake in a 325-degree F. oven for 18 to 20 minutes or until bottoms of cookies are very lightly browned. Cool on cookie sheet for 1 minute. Transfer to wire racks and cool completely.
To make the icing, stir together sifted powdered sugar and enough milk to make an icing that is of piping consistency. Divide the icing into 3 small bowls. Tint 1 portion pink. This will be for the arms and the mouth. Tint another portion green. This portion is used for the broom. Tint the remaining portion orange; this will be for the nose. Place each color in a small, heavy plastic bag. Snip off a corner in the bag to make a small opening.
The hats are made out of gumdrops. Sprinkle the work surface with a little granulated sugar. Flatten a large gumdrop to a thin oval shape that is about 1-1/2x1 inches with a rolling pin. You may also need to add a little sugar to the surface of the gumdrop to keep it from sticking to the rolling pin. With your fingers, shape the oval into a cone and pinch the edges together. Roll up the bottom edge of the cone to form a hat brim.
For each scarf, cut rolled fruit leather into 3-inch-long thin strips. Carefully tie the strip around the snowman,s neck. Attach the gumdrop hat to the head with a little icing. Use the orange icing to add a carrot nose. Use the pink icing to add a mouth, and arms to each cookie. Use the green icing to add a broom to the side of the body.
Makes 24 cookies.
Make-Ahead Tip: Bake and cool cookies completely; do not decorate. In an airtight or freezer container, arrange cookies in a single layer; cover with a sheet of waxed paper. Repeat layers, leaving enough air space to close container easily. Seal, label and freeze up to 1 month. Thaw and decorate as above.
These snowman cookies are fun for kids to shape and decorate.