Preheat oven to 350° F and line a baking sheet with parchment paper.
Add softened butter to a large mixing bowl or to the bowl of a stand mixer with the paddle attachment.
Beat until the butter on medium high speed for approximately 30 seconds until fluffy.
Add the vanilla extract and reduce the speed to low speed.
Slowly add the powdered sugar and flour and beat on low until completely incorporated, stopping to scrape down the sides as you blend.
Add milk 1 tablespoon at a time until the dough forms into a ball.
Place the dough onto a lightly floured surface and roll it to ¼” thick.
Cut out your desired shapes and place the cookies on the parchment lined baking sheet.
Place the cookie sheet in the freezer for 15 minutes. DO NOT skip this step or the cookies will not hold their shape.
Once the cookies have chilled, bake them for 12-15 minutes, or until the bottoms are slightly brown.
Allow the cookies to cool completely on the tray before decorating.
For the Icing
Combine the powdered sugar and milk in a medium bowl and blend until smooth.
Add a few drops of food coloring and blend again. Repeat until desired color is achieved.
Add the the frosting to a piping bag or plastic zip closure baggie and cut a small opening in the corner or tip.
Apply the icing to the cookies as desired, followed by sprinkles while the icing is still wet.
Allow the icing to set before storing.
Store in an airtight container in the refrigerator for up to 3-4 days.Make sure to measure using the scoop and level method so cookies do not come out too dry.Substitute half-and-half or heavy cream for milk.Use store-bought cookie icing if preferred.