Start by creaming your butter and sugars together until the mixture is light and fluffy. Divide this base into separate bowls if you plan to make multiple flavors. For the gingerbread portion, mix in the molasses and spices, while the shortbread portion stays simple with flour and alcohol-free vanilla. Ensure all dry ingredients are sifted to avoid lumps in your holiday treats.
Wrap each type of dough in plastic wrap and place them in the refrigerator for at least one hour. This step is crucial because it prevents the cookies from spreading too much in the oven and helps develop a deeper flavor. Chilled dough is also much easier to handle when you are using festive cookie cutters like stars or trees.
On a lightly floured surface, roll out your dough to about a quarter-inch thickness. Use your favorite holiday cutters to create a variety of shapes. For thumbprint cookies, roll small balls of dough and press your thumb into the center to create a well for the jam. Arrange everything on baking sheets lined with parchment paper.
Preheat your oven and bake the cookies in batches. Most cookies will take between 8 to 12 minutes depending on their size. Watch for the edges to turn a very light golden brown. It is important to let the cookies sit on the hot baking sheet for a few minutes after removal so they can set properly before you move them to a cooling rack.
Once the cookies are completely cool, you can add decorations like powdered sugar dusting or chocolate drizzles. To assemble the Christmas Cookie Box, use a sturdy container and place cupcake liners or parchment paper dividers inside. Group the different types of cookies together to create a beautiful, organized look that highlights the variety of your hard work.