Box of Chocolates Valentine Sugar Cookies with Buttercream

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Valentine’s Day is approaching so I have a fun tutorial for these heart shaped box of chocolates sugar cookies.

These Valentine sugar cookies are made with a chocolate fudge sugar cookie recipe. The chocolate base is important for two reasons:

  1. The overwhelming flavor of Valentine’s Day is obviously chocolate. 
  2. The chocolate base allows you to skip a step of covering the cookie with a base layer of brown frosting. Simply begin to pipe the chocolates!

Do you sell buttercream sugar cookies? If so, these heart shaped box of chocolates sugar cookies are a perfect Valentine’s Day cookie set.

One cookie in the set consists of the top of the box, red with a bow, and the other is the box of chocolates. Such a perfect pair!

It’s also nice because one cookie will show off your skillset while the other cookie is quick & easy.

valentine cookie sets ideas

Let’s get started on these chocolate cut out sugar cookies for Valentine’s Day!

This post may contain affiliate links to Amazon, which means I may receive a commission, at no extra cost to you, if you make a purchase through a link. Please see my full disclosure for further information.*

Part 1: Gathering the Supplies for the Box of Chocolates Sugar Cookies

To decorate these buttercream Valentine sugar cookies, you will want to gather:

Part 2: Baking the Cookies and Setting up the Icing Bags

Use the recipe card below for the sugar cookie and buttercream frosting recipes.

Valentine's Day Box of Chocolates Cut Out Cookies

These delicious brownie chocolate cut out cookies are topped with a soft vanilla buttercream frosting and decorated like a box of chocolates. Gift your loved ones the perfect Valentine sugar cookie!
Print Pin Rate
Course: Dessert
Cuisine: American
Keyword: Chocolate Cut Out Cookies, Cut Out Cookies, Sugar Cookies, Valentine Sugar Cookies
Prep Time: 1 hour
Cook Time: 10 minutes
Decorating Time: 4 hours
Total Time: 5 hours 10 minutes
Servings: 18 cookies, depending on the size of your cookie cutter


  • Stand Mixer with Paddle Attachment
  • Mixing Bowl
  • Rolling Pin
  • Heart cookie cutter
  • Cookie Sheet
  • Icing Bags
  • Couplers
  • Decorating Tips
  • Palette Knife


Chocolate Fudge Cut Out Sugar Cookies

  • 3 cups all purpose flour
  • 1 package Chocolate Fudge instant pudding mix 3.9 ounce package
  • 1/2 cup cocoa powder
  • 1 cup cold salted butter
  • 3/4 cup granulated sugar
  • 1/4 cup dark brown sugar packed
  • 1 egg
  • 1 tsp vanilla extract
  • 1-3 tbsp canola oil, or preferred light tasting oil see instructions

Crusting Vanilla Buttercream for Sugar Cookie Decorating

  • 1 cup unsalted butter room temperature
  • 4 cups powdered sugar
  • 1 tbsp vanilla extract
  • 1-3 tbsp whole milk, half & half, cream, or water
  • brown, orange, and red gel food dye see section 2 for color mixing notes
  • Valentine's Day sprinkles


Chocolate Fudge Cut Out Cookies

  • Preheat your oven to 350 degrees Fahrenheit and take out the cup of unsalted butter to begin to come to room temperature. The unsalted room temperature butter is for the buttercream.
  • In a large mixing bowl, mix your flour, cocoa powder, and Chocolate Fudge pudding mix together. When measuring the flour, make sure to scoop up the flour with a spoon and add it to your measuring cup, one spoonful at a time. This helps obtain the correct amount of flour without needing to weigh it. Once you have a cup, level it out by running a knife across the top of the measuring cup.
  • In your electric mixer, combine the white and brown sugars with the butter using the paddle attachment until they are creamed together.
  • Add in your egg, 1 tablespoon canola oil, and vanilla extract and mix to combine.
  • Slowly add in the flour, cocoa powder, and pudding mixture to the wet ingredients and combine. The combined mixture will be crumbly but still form a ball if picked up and molded into a ball. If it is too crumbly, add in another tablespoon of canola oil.
  • On a floured surface, roll out the dough to about a 1/4 of an inch thick & cut out your cookies. A great tip is to flour your rolling pin. Transfer the cut out cookies to a baking sheet lined with a  silicone mat or parchment paper.
  • Bake for 9-10 minutes and let cool on the baking sheet. The dough will be done when the center of the dough doesn’t look wet. It is better to undercook the cookies than to overcook them, as it will be difficult to watch for burns with these dark sugar cookies.
  • Optional but highly suggested: Place the cooled cookies into an airtight container and freeze them overnight. Remove the container from the freezer 1 hour before decorating for soft brownie chocolate cut out cookies.

Crusting Buttercream

  • In a stand mixer with the paddle attachment, cream the unsalted room temperature butter until light and fluffy, about five minutes on high.
  • Add in the powdered sugar, vanilla extract, and one tablespoon of milk. Cover the mixer with a paper towel or clean tea towel and mix on low until combined. If the frosting is too thick (thicker than smooth peanut butter) add more milk, up to two more tablespoons.
  • Follow the instructions in Part 2 for how to divide up the frosting, dye it, and prepare the icing bags.

Decorating the Valentine Sugar Cookies

  • Follow the instructions in Part 3 for decorating the sugar cookies.


Make your buttercream icing according to the recipe and separate it into three equal bowls:

      • dye one bowl a dark brown
      • dye another bowl a milk chocolate brown – mix some orange into the brown
      • dye another bowl red

Divide the dark brown frosting into two icing bags – one with a coupler and one with the Wilton #101 or GG #101s tip in it.

Place the remaining colors into their own icing bags, each with a coupler. You don’t need to add any tips to the couplers yet.

Part 3: Decorating the Box of Chocolates Cookies with Buttercream Frosting

Check out the video tutorial showing the overall process for decorating the buttercream Valentine sugar cookies then follow the step-by-step photo series tutorial below.

How to Decorate the Box of Chocolates Cookies with Buttercream

how to decorate valentine sugar cookies box of chocolates

  1. Use the tip #5 on the red icing bag to outline the heart cookie. valentine sugar cookies box of chocolates
  2. Remove/rinse/dry the tip #5 from the red and add it to the milk chocolate brown icing bag. Pipe a circle toward the bottom of the heart, making sure to leave room around the edges to pipe the paper. valentine sugar cookies box of chocolates
  3. Use the icing bag with the 101 tip to pipe the paper around the chocolate. To do this, hold the decorating tip perpendicular to the cookie with the thin side of the tip facing up. Make sure to wiggle the tip back and forth to create a wave. Use the palette knife to smooth or add texture to the candy. valentine sugar cookies box of chocolates valentine sugar cookies box of chocolates valentine sugar cookies box of chocolates
  4. Repeat steps two and three to fill the whole cookie. You can use the dark brown with the tip #5 on it to create some of the chocolates too, still using the other dark brown icing bag with the 101 tip to outline it. valentine sugar cookies box of chocolates valentine sugar cookies box of chocolates valentine sugar cookies box of chocolates
  5. Add some sprinkles to some of the chocolates. valentine sugar cookies box of chocolates
  6. Use the tip #2 on the dark brown and the milk chocolate brown to draw a squiggly line over some of the chocolates to represent the melted chocolate on top. valentine sugar cookies box of chocolates

How to Decorate the Top of the Box of Chocolates Cookies with Buttercream

  1. Use the tip #5 on the red icing bag to outline and fill in the heart cookie. Smooth the frosting out with the palette knife and clean up the edges. valentine box of chocolates cookies
  2. Replace the tip #5 on the red icing with the tip #44. Pipe a straight line along the cookie from one side to another, starting at the top of the left side of the heart. valentine box of chocolates cookies
  3. Pipe the bow on top of the line with the tip #44. valentine box of chocolates cookies

These Valentine sugar cookies are perfect for selling and for bringing to a Valentine’s Day party.

If you’re bringing these cookies to a party, make sure to read my post on how to package and transport buttercream sugar cookies.

Save the Tutorial for These Valentine Sugar Cookies

Use the image below to pin this tutorial for these box of chocolates sugar cookies to your Valentine board on Pinterest. Alternatively, use any of the social share icons on the top of the page to share it to your favorite social media site.

valentine sugar cookies box of chocolates sugar cookies


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