In advance: Prepare and roll out dough. Cut cookies using boot cutter from set. Bake and cool cookies. Outline using tip 2 and full-strength black icing. Flow in with thinned black and orange icing. Let dry 24 hours.
Add details using tip 2 and full-strength icing. Outline buckle, outline and fill-in heel and sole; pipe dot eyelets. Sprinkle on colored sugars. Pipe outline laces. Attach to candy sticks with melted candy.