Bake cupcakes as directed on cake box. IMPORTANT - Allow to cool completely before icing and decorating.
Here's where the fun begins.
Prepare the cupcakes for assembly by slicing an angled hole to one side of the cupcake where the Milano cookie gets inserted.
The Milano cookies are used for the sole of the shoe. The rolled wafer cookies are used as the heel.
Melt 2-3 bars of chocolate in the microwave only until melted.
Here's where a light touch is needed. With a serrated knife carefully and lightly slice the wafer cookie in half. My heels measured almost 2 1/2". Next you will slice the tip of the cut end at an angle. This is so the Milano cookie rests at the angled part. It's ok to not understand this until you see how the heel fits to the angle of the cookie. You may need to adjust the length by shaving the angled end down little by little.
Dip the flat end of the wafer cookie into the melted chocolate and stand in a bowl to dry. Sometimes I needed to prop them up. To prevent them from sticking to the dish - before they dry completely lay heels on their side with chocolate dipped end hanging over the edge. I use a cutting board.
Frost cupcakes and using the tip of your knife feel where the hole is for the Milano cookie. Insert cookie.
Dip the angled end of the wafer cookie in chocolate and affix to the sole of the Milano cookie. You may need to dip it in chocolate a few times to get enough chocolate on the end. I think I dipped it about 3 times. Let it rest to form a bond. Do this with all the cupcakes because by the time you are ready to decorate the first cupcake's heel should be secured.
Let your imagination run wild with decorating.