Line two cookie sheets with parchment paper then set aside.

In the bowl of a stand mixer fit with the paddle attachment or with a hand-held mixer, cream together the butter and sugar until light and airy. About 2 minutes.

Add the vanilla and egg yolk to the butter mixture. Mix until well combined.

Add the flour and salt to the butter mixture and mix until it begins to resemble crumbly pieces.

Use your hands to bring the dough together into a ball.

Roll the dough out onto a piece of parchment paper. The dough will stick to the rolling pin so place an additional piece of parchment paper over the dough to prevent the dough from sticking and breaking. The dough should be rolled out to about ⅛″.

Transfer the rolled-out dough to a cookie sheet and let chill and firm up in the fridge for about 15-20 minutes.

Once the dough has chilled and become easier to work with, cut out as many circles as you can (I used a 4" circle cookie cutter). Re-roll the scraps and continue to punch out circles until all of the dough is used up. Cut oval eyes out of half of the circles to make the eyes for our Jack Skellington faces.

Place the cookies 1 ½" apart onto the prepared cookie sheet then bake at 350 degrees for 8 minutes or until just golden brown on the edges. Transfer the cookies to a cooling rack to cool completely before assembling and decorating.

Once our cookies have cooled, we can make the icing for decorating. Whisk together the confectioner's sugar, vanilla, and water making sure to add the water a little at a time. While the icing is still a thicker consistency, remove about 1-2 Tbsp. of dough and dye it black. This is what we'll use for the mouth. Add a few more drops of water to the remaining uncolored icing to make it a bit thinner. This is what we will use for the face.

Place about 1-2 tsp. of jam on the bottom side of the un-carved cookies then spread the jam out almost to the edges. Place a cookie with the eyes cut out on top.

Decorate the faces by piping or spreading the icing on the face then piping a smile and nose.

Repeat these steps for each one until every cookie is decorated.