Preheat your oven to 350°F and prepare a baking sheet with parchment paper. While the oven heats, sift the 1.5 cups of powdered sugar for the icing (removing lumps ensures a smooth, professional-looking glaze), and measure out all your cookie dough ingredients: 2 cups flour, 1 tsp vanilla extract, and 2 tbsp milk. Having everything ready before you start mixing makes the process seamless and prevents the butter from over-softening.

Beat the softened butter for about 30 seconds until it becomes light and fluffy—this aerates the dough and creates a tender cookie. Add the vanilla extract and mix briefly to combine. Add the sifted powdered sugar and flour together, mixing until just combined, then gradually add the 2 tbsp milk one tablespoon at a time until the dough forms a cohesive ball. I like to add the milk slowly because humidity varies day-to-day, and you want just enough to bring everything together without making it sticky. On a lightly floured surface, roll the dough to about ¼-inch thickness and cut into your desired shapes using cookie cutters. Transfer the cut cookies to your prepared baking sheet.

Place the baking sheet in the freezer for 15 minutes before baking—this prevents the cookies from spreading too much and helps them maintain sharp edges. After chilling, bake for 12-15 minutes until the bottoms are light golden brown; the tops should still look pale or barely set. This keeps them tender and shortbread-like rather than crispy. Remove from the oven and let the cookies cool completely on the baking sheet for at least 10 minutes before transferring to a wire rack.

While cookies cool, prepare the icing by whisking together 1/2 cup powdered sugar and 3 tbsp milk until completely smooth and pourable—the consistency should be thin enough to spread or pipe but thick enough to cling to the cookie. Add a few drops of red or pink food coloring if desired and stir until the color is evenly distributed. Transfer the icing to a piping bag with the corner snipped off, or use a small spoon to drizzle. Once cookies are fully cooled, pipe or drizzle the icing over each cookie in your preferred pattern, then immediately add sprinkles while the icing is still wet so they stick. I find that working quickly while the icing is tacky ensures the sprinkles stay put, giving you that professional bakery finish.