Our High Heel Cupcakes

Creating these high heel cupcakes last spring with my daughter-in-law, Amy, was so much fun.   This post is dedicated to Amy who passed away October 2014. I will always treasure the time we shared.


High heel cupcakes are a great idea for a girl’s birthday party or bridal shower.  You can can even have the party participants decorate their own high heel cupcake. At the end of this post I included a technique to package high heel cupcakes for delivery.

Items needed:

.Pirouettes cookie sticks

.Milano cookies – any flavor

.White melting chocolate

.Colored sugars and decorative candies

.Baked cupcakes in cupcake liners – allow to cool before icing

.White Icing – this works better is icing is cold.

.Wax paper – place on table to make clean up easier

.Saucers or heavy cardboard covered with wax paper or foil to position and hold the high heel cupcakes during assembling and drying

.Microwavable small bowl to melt white chocolate

.Bowls to place different colored sugars into for coating cupcakes and cookies

.Butter knives



If you can, use special cupcake liners called ColorCups Baking Cups from Wilton. These cupcake liners have a foil lining that prevents the cupcake liner from turning dark or absorbing grease. Otherwise, use regular cupcake liners to bake. You can add another matching cupcake liner over a baked cupcake liner to add to the look of the presentation. You may need to secure the extra liner to the original baked cupcake liner with melted white chocolate.

You can make your own colored sugars by adding a few drops of food coloring to regular granulated sugar and blend until color is mixed.

You can skip several steps below if you decide to have plain soles for the shoes.  Just do not cover the Milano cookies with white chocolate and colored sugar. You will still need white chocolate to use as ‘glue’ for constructing the high heels.

cup cake liners  2014-02-22_12-50-04_203

Step 1:

Cut Pirouettes cookie sticks in half at an angle so that you have one half stick for each cupcake. These will be the heel of the cupcake. You will need one per cupcake.

Step 2:


You will need one Milano cookie for each cupcake to create the sole of the high heel.  Place the Milano cookies onto wax paper on a flat surface. Melt 3 squares of white chocolate in the microwave on high 45 seconds. Remove from microwave and stir. If not completely melted, return to microwave for 30 seconds, remove, and stir. Repeat process if needed until white chocolate is melted. Do not overcook.

With a butter knife, smooth a small amount of melted white chocolate onto one side of the Milano cookie. Repeat for the other cookies. Allow the white chocolate to cool and solidify.

milano 1 side

Step 3:

Once the white chocolate has hardened on the one side of the cookies, turn the cookies over.

Step 4:

With a knife, carve out a circle near one end of the cookie (not the iced side). You may have to carve a little of the cookie away at a time until the Pirouettes cookie stick slant end will fit into the circle. Repeat this on all on the cookies.

milano cut milano side 2

Step 5:

With a knife, cut away a portion of each cupcake. This will be the area you secure the cookie heel.

cake cut

Step 6:

Ice your cupcakes with a good mound of cold frosting. You can use a spoon, a plastic decorating bag, or a heavy freezer plastic bag to add the icing to the cupcakes.

cupcake iced

Step 7:

Dip the frosted cupcake into colored sugar making sure you cover the sides of the frosting. Set aside.

sugar cupcake

Step 8:

Melt 2 squares of white chocolate in the microwave on high 30 seconds. Remove from microwave and stir. If not completely melted return to microwave for 30 seconds,  remove, and stir. Repeat process if needed until white chocolate is melted. Do not overcook.

Allow the melted chocolate to cool a little. This will help prevent the Milano cookie filling from melting.

Holding the Milano cookie with the white chocolate side up, with a knife smooth a small amount of slightly cooled melted white chocolate all around the edges of the cookie. While the white chocolate is still warm, dip or spoon colored sugar onto the edges. Allow to cool.

2014-02-22_12-50-06_951   milano sugar1

Step 9:

Dip the slanted end of the Pirouettes cookie stick in melted white chocolate. Secure the white chocolate covered slanted end of the Pirouettes cookie stick onto the cookie sole. Hold until the melted chocolate has cooled and the Pirouettes cookie is  secured.

milanpir milanopira

Step 10:

Spoon melted white chocolate into the cut away area of the cupcake. This will serve as glue to hold your cookie sole in place.

cupcake iced

Insert the Milano white chocolate and sugar side up cookie into opening. IMPORTANT – make certain the carved hole on the back of the sole is not inserted into the white chocolate glue. Continue holding the cookie in place.

Step 11

Check cupcake and cookie before while chocolate completely cools to see if you need to sprinkle on any more matching colored sugar.

milano sugar 2

Step 13:

After the sole has completely cooled, check the Pirouettes cookie heel. If the heel is lose, add more melted white chocolate to securely ‘glue’ the heel to the sole.



Packaging High Heel Cupcakes for Delivery

Hint: Always, place your cake boxes on a flat surface in your vehicle for traveling. Non-skid shelf liner is great to place on a floor or seat of your vehicle to prevent cakes boxes from shifting. If you do not have floor board space and your car seat slants, use a towel to even out the car seat. Make certain the cake boxes will not fall off the car seat in case of a sudden slam on the brakes by placing large boxes or other items in the open floor space in front of the seat.

Individual Boxes

Items Needed:

Boxes at least 3 ½ x 4 x4 inches

Cake boards

One Pirouettes cookie stick



Knife for cutting board

Step 1:

Set an assembled cupcake box on top of a cake board. Using a pencil or pen, draw around the box edge and cut the board with scissors. Use this as a template to cut other cake boards to fit into the bottom of the box.

Step 2:

Using the Pirouettes cookie stick placed flat onto one end and middle ways of one of the cut boards, draw around the cookie stick to form a circle. With a knife, cut away the inside of the circle. Test the cut out with the cookie stick to see if you need to cut away any more of the board.

Step 3:

Place the board into the bottom of the box.

Step 4:

Carefully place your high heel cupcake into the box making sure the cookie stick fits inside of the cut hole.

Step 5:

Gently tuck napkin around and under the high heel cupcake to make certain the cupcake will not shift inside the box.

Step 6:

Close the close lid.




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