Stiletto Cupcakes

Anyone who knows me well knows that I have a shoe problem.  At last count, I was up to seventy-five pairs, not counting flip-flops (which are their own addiction).  That’s after I pared down the collection to make room in my closet.  I know that some of you are amazed at anyone owning seventy-five pairs of shoes, but I’d like to point out that Imelda Marcos had about 2700 pairs.  I envy her sometimes.  But, I only have two feet to wear them on and only so much storage space, so I managed to pare down and I’ve managed to not buy any new shoes for a while.

Enter my birthday.  It’s kind of  a birthday tradition for me to treat myself to a pair of shoes, usually of the high-heel, strappy, impractical variety.  I’ve declared a moratorium on buying more stuff I don’t need, so I decided this year, I’d skip the shoe sale and bake some cupcakes instead.  So last Monday, for my birthday, I baked and frosted and decorated twenty-four cupcakes, which gave me twelve pairs of adorable new shoes that I didn’t have to make space in the closet for.  I think this was more fun.

I’m not going to lie, these cupcakes take time, and effort.  I spent a few hours assembling all of these, but I’m glad I did.  Friends and family loved them, and spreading joy to friends and family is something my actual shoes rarely manages to accomplish.  These would be perfect for a shower, bachelorette party, or birthday and I already have requests to make them again for such occasions.  The sky is the limit with decorations-  browse the candy or cake decorating areas of a store and see what inspires you.  My only word of caution is that the cupcake wrapper itself is part of the design, so spend a little extra and use grease-proof or glassine cupcake wrappers.  I ordered mine from Bake It Pretty, and Sur La Table also has a nice selection.  You can either frost the graham cracker “arches” with the buttercream frosting, or you can dip the graham cracker in melted chocolate that matches the “shoe.”  I chose to frost them so that I didn’t have six different colors of chocolate hanging around the house.  I’d say either method is equally labor-intensive, so do what you prefer.

Stiletto Cupcakes


  • 24 cupcakes, using your favorite recipe (I used Annie’s Eats vanilla cupcakes), baked in decorative wrappers
  • 1 recipe buttercream frosting
  • assorted food coloring, in colors of your choice
  • assorted candy, sprinkles, and toppings that coordinate with the cupcake wrappers
  • 12 stick-shaped cookies (such as Pepperidge Farm Pirouette cookies)
  • 12 graham crackers
  • melting chocolate (any color is fine, unless you want to dip the graham crackers in it)
Divide the frosting into bowls according to how many styles of cupcake you’re making. I was making six different styles, so I had six bowls.
Color each bowl of frosting using food color of your choice (I made yellow, pink, teal, purple, black, and left one bowl white).
Break each graham cracker in half so you have 24 squares.
Cut two corners of each graham cracker square off, diagonally from each other.  You should have a shape that looks sort of like a neck tie.
If desired, you can also carefully round one end of the graham cracker cut-out.  I did this for some, but not all.  I don’t think it made a big difference on the first few pairs, so I skipped it on the rest.
Frost the graham cracker “arches” to match the cupcakes they’ll go with.  You only need to frost the top and sides.  If you’re decorating the edges of the arch, now is the time to do that (as is the case with the yellow and pink cupcakes I made- I dipped them into their toppings at this point).
Let the graham crackers sit on waxed paper while you frost and decorate the cupcakes, to give the frosting a chance to harden a little.  If you’re using chocolate melts, dip them and let them sit on waxed paper in the freezer until the chocolate sets.
Frost each cupcake to match its wrapper, and decorate as desired.
  • For the pink cupcakes, I added red food coloring to some shredded coconut in a plastic bag and squished the bag until the color was evenly distributed.  I then dipped the frosted cupcake into it.
  • For the black/ leopard cupcakes, I frosted them black, and then used toothpicks to secure black licorice around the edges.
  • For the yellow cupcakes, I frosted them yellow, then sprinkled multi-colored nonpareils on top.
  • For the teal cupcakes, I frosted them teal and used a piping bag and tip to pipe the design on.
  • For the white cupcakes, I frosted them white and then pressed flower-shaped gummy candy onto them.
  • For the purple cupcakes, I frosted them purple and pressed M&M’s candy into the frosting.
To assemble the cupcakes, cut the Pirouette cookies in half, and then cut one end of each on an angle.
Push the frosted graham cracker arch into the back of the cupcake.
Dip the angled end of the Pirouette cookie into melted chocolate and put it under the graham cracker to stabilize it.  Hold it in place for a few seconds.  The Pirouette should not be supporting the weight of the graham cracker arch, the arch should be pushed far enough into the cupcake that it stays up on its own.
Wait until the chocolate holding the “heel” on has hardened, and then serve.
Makes 24 high-heels.
Source:  cupcakes, Annie’s Eats; frosting, Confections of a Foodie Bride; high heel directions, How Does She?


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