In a mixing bowl, use a stand mixer or hand mixer to blend 1 cup of softened butter and 2/3 cup of granulated sugar until the mixture becomes fluffy and pale.
Next, add in 1 room temperature egg and 1 teaspoon of vanilla extract. Give it a good mix until everything is nicely incorporated.
Now, sift in 2 cups of all-purpose flour and sprinkle in 1/4 teaspoon of salt. Mix on low speed just until combined for a tender dough.
Pour in 2 teaspoons of milk and blend further until the dough reaches a piping consistency. If needed, add a little more milk but keep it minimal.
Move the dough into a piping bag fitted with a large tip. Pipe swirls about 2 inches apart on a baking sheet (skip parchment paper!).
Chill the piped cookies in the refrigerator for about 15-20 minutes to help hold their shape while baking.
Preheat the oven to 350°F.
Bake cookies for approximately 15 minutes until the edges turn golden brown.
Allow the cookies to cool on the baking sheet for about 10 minutes, then transfer them to a wire rack to cool completely.
While cooling, melt the chocolate using a double boiler or microwave, stirring every 20 seconds until smooth.
Dip two-thirds of each cookie into the melted chocolate and place them on parchment paper. Sprinkle with toppings and let the chocolate set completely.