Prep your station. Line a baking sheet with parchment paper. Unwrap the chocolate kisses and set them in a small bowl.
Place your cookies flat side up on the lined tray.
Melt the chocolate. Add chocolate chips or melting wafers to a microwave-safe bowl. Microwave in 20–30 second bursts, stirring between each round, until smooth. If the chocolate seems thick, stir in 1 teaspoon of oil to loosen.
Attach the hats. Use a small spoon or piping bag to dab a pea-sized amount of melted chocolate in the center of each cookie.
Press a chocolate kiss onto the chocolate. Hold for a few seconds so it sets and stands upright.
Create the hatband. Once the chocolate base has set slightly (1–2 minutes), pipe a thin ring of colored icing around the base of each chocolate kiss. This becomes the witch hat’s band.
Add the buckle. While the icing is still soft, press a mini M&M, sprinkle, or candy pearl onto the front of the hatband.
This little pop of color makes the design stand out.
Optional drizzle. For extra flair, drizzle a bit of melted chocolate or white chocolate over the cookie base. Add Halloween sprinkles before the drizzle sets.
Let them set. Transfer the tray to the fridge for 10–15 minutes, or leave at room temperature for 30–45 minutes, until everything is firm to the touch.
Plate and serve. Arrange on a platter or tiered stand. If transporting, keep the cookies on parchment to avoid smudging the icing.