1. Preheat Your Oven

Start by preheating your oven to 350°F (175°C). This ensures that your cookies bake evenly and don’t spread too much.

2. Mix the Dough

• In a large mixing bowl, combine the flour and powdered sugar. Whisk them together to make sure they’re fully incorporated.
• Cut the softened butter into small cubes and add it to the flour mixture. Using a pastry cutter or your hands, work the butter into the flour until the mixture resembles coarse crumbs. You can also use a stand mixer with the paddle attachment on low speed for about 3-4 minutes.
• Add vanilla extract and salt. Mix just until the dough comes together. You want it to be soft, not too sticky or crumbly. If it’s too dry, add a tiny splash of milk (a teaspoon at a time) until it reaches the right consistency.

3. Chill the Dough

Wrap your dough in plastic wrap and chill it in the refrigerator for 30 minutes. This step is key to getting that perfect shortbread texture and preventing the cookies from spreading too much while baking.

4. Shape the Cookies

Once your dough has chilled, remove it from the fridge. Roll it out onto a lightly floured surface to about 1/4-inch thickness. Use a cookie cutter to cut out your desired shapes. I love using a star or tree cutter for that extra holiday cheer, but a simple round cutter works just as well!

5. Bake the Cookies

Place the shaped cookies onto a baking sheet lined with parchment paper. Make sure to leave a little space between each cookie, as they will slightly expand. Bake in the preheated oven for 15-18 minutes, or until the edges are golden brown. Keep an eye on them, as oven temperatures can vary!

Once they’re done, remove the cookies from the oven and let them cool on the baking sheet for a few minutes before transferring them to a wire rack to cool completely.

6. Dip in Chocolate

While your cookies are cooling, it’s time to melt the chocolate. In a heatproof bowl, melt your chocolate chips using either the microwave (in 30-second increments) or over a double boiler. Stir until smooth and creamy. Be careful not to burn the chocolate!

Once the cookies are completely cooled, dip half of each cookie into the melted chocolate, then gently shake off any excess. Place them on parchment paper to set.

7. Decorate

Before the chocolate sets, sprinkle your cookies with holiday-colored sprinkles or crushed candy canes for a festive touch. If you’re feeling extra fancy, drizzle some additional melted chocolate over the cookies for an added decorative flair.

8. Let the Chocolate Set

Let the chocolate-coated cookies sit at room temperature for about 30 minutes or until the chocolate has fully set. If you’re in a hurry, you can refrigerate them for about 15 minutes.