In advance: Make cookies. Prepare and roll out dough. Cut using shoe cutter from set. Bake and cool cookies.
Tint royal icing and 1/4 oz. fondant rose per treat. Outline shoe with tip 3 and full-strength icing; flow in with thinned icing. Let dry 24 hours. Make fondant ribbon rose; attach using damp brush. Cut Lollipop Sticks into 3 in. lengths; attach 2 to back of shoe using melted candy, leaving 1 1/2 in. extended to insert into cake. Let set.
Bake and cool 1-layer cake using firm textured batter such as pound cake. Trim to 3 1/2 x 3 1/2 x 1 1/2 in. high; trim and taper edges for pillow shape. Prepare for rolled fondant. Roll out white fondant 1/8 in. thick. Cut a 5 1/2 in. square. Use Cutter/Embosser with straight wheel to score lines 3/4 in. apart. Attach to cake; flip cake over onto foil-wrapped cake circle. Repeat to cover second half. Brush outer edges with damp brush and pinch closed; trim away excess fondant. Attach Sugar Pearls on top where lines intersect.
Use Decorative Press with 3-hole insert to make legs. Cut two 7 in. lengths; twist together and attach to one side using damp brush. Repeat for other three sides. For each tassel, cut five 1 in. long ropes; pinch top ends together and attach at corners. Brush whole pillow and shoe with Pearl Dust. Insert shoe.
A timeless and versatile technique, the ribbon rose can elevate the look of any cake or treat. Ribbon roses can be made in many sizes for variation. They can be used as simple cake decorations and also to dress up cupcakes.