In a large bowl, beat the softened butter and granulated sugar together until the mixture is light and fluffy. This usually takes about three to five minutes. Add the eggs one at a time, followed by the alcohol-free vanilla, ensuring everything is well combined before moving to the next step.
Gradually stir in the flour and salt until a soft dough forms. At this point, you can divide the dough into separate bowls if you want to create different flavors. For a chocolate version, mix cocoa powder into one portion of the dough. Wrap the dough portions in plastic wrap and chill in the refrigerator for at least thirty minutes.
Preheat your oven to 350 degrees Fahrenheit. Roll out the dough and use holiday-themed cutters for some, and roll small balls for thumbprints or crinkle cookies for others. Place them on parchment-lined baking sheets and bake for 10 to 12 minutes, or until the edges are just barely golden. Let them cool completely on a wire rack.
Once cooled, fill the centers of your thumbprint cookies with jam. Melt the chocolate chips in a microwave-safe bowl and drizzle over the shortbread or dip the ends of the cookies into the chocolate followed by a sprinkle of crushed peppermint. Dust some of the plain shapes with powdered sugar for a snowy effect.
Line your boxes or tins with festive parchment paper or cupcake liners. Group the cookies by type to keep the flavors distinct and prevent the softer cookies from making the crisp ones soggy. Fill any small gaps with loose candies or nuts to make the box look abundant and professionally styled.
