Make cookies one day in advance. Prepare dough and roll out following recipe directions. Use shoe cutter from set to cut shape. Bake and cool cookies.
Decorate cookies. Prepare Color Flow icing following recipe directions. Tint portions black and yellow. Use tip 3 and full-strength black icing to to outline cookie. Use thinned black icing in cut disposable decorating bag to fill in. Let set overnight.
Use tip 2 and full-strength black icing to pipe laces. Use tip 5 and full-strength yellow icing to pipe buckle. Use finger dipped in cornstarch to pat down.
Make cake circles. Prepare batter following recipe directions. Tint batter orange. Bake and cool cake according to pan package directions. Use knife to level cakes 1/2 in. high. Use smallest round (1 3/4 in.) cutter from set to cut four cake circles per treat pop.
Assemble treat pops. Prepare buttercream icing following recipe directions. Tint violet. Push cake circles into bottom of treat pop. Use tip 2A and violet icing to pipe a swirl of icing from back edge following the curves of the container, then filling the center. Repeat to add three more layers of cake and icing.
Add cookie. Use knife to trim lollipop stick to 5 in. Melt white Candy Melts candy according to package directions. Use melted white candy to attach lollipop sticks to back of cookies. Chill until set 3 to 5 minutes. Insert lollipop stick into center of treat pop.