In the bowl of your mixer, beat butter on medium speed for about 30 seconds. Add sugar to butter and continue to beat until combined.
Beat in milk and vanilla, scraping down sides until all is combined.
Next mix in as much of the flour as you can with the mixer. Stir in any remaining flour by hand. Remove 1 cup of the dough and place in a separate bowl . With the remaining dough, tint red with food coloring gel in mixer.
For each Santa (this should make 10-12 cookies), shape red dough into twelve- 1-inch ball and sixty -1/2-inch balls(one 1-inch red dough ball, and five ½-inch red dough balls per Santa cookie.)
Shape plain dough into twelve- ¾-inch ball and forty-eight- ¼-inch balls (one ¾-inch plain dough ball, and four-1/4 inch plain dough balls)
Line 2 baking sheets with baking mat or parchment paper.
Place the red 1-inch ball on a baking sheet, flattening the dough ball until about ½ inch thick. Attach the plain ¾-inch ball for head, flattening until ½ inch thick.
Next, attach four of the red ½-inch balls for arms and legs and then attach the plain ¼-inch balls for hands and feet. Pinch the remaining ½-inch red ball into a Santa hat and attach to head.
Repeat steps to create the rest of the Santas. Add the mini-chocolate chips as eyes and buttons.
Bake Santa cookies for 12 to 15 minutes until edges are lightly browned.
Let the cookies cool on baking sheet. Be careful because the are extremely fragile. Once cooled, gently move to a wire cooling rack.
To create beard, put frosting in a piping bag with a small star tip (recipe below). Attach the red hot for the nose. Let sit until frosting sets.
For Frosting-
In the bowl of you mixer, beat together shortening and vanilla for around 30 seconds. Gradually mix in around ½ cups of the confectioners' sugar until smooth. Next beat in 1½ tsp. milk. Continue to mix in remaining confectioners' sugar until the consistency for piping.
Recipe by 2 Sisters 2 Cities at https://www.2sisters2cities.com/2013/12/1-roly-poly-santa/