Make hat two days in advance. For each treat, reserve a ball of white fondant, 1/2 in. dia. Tint remaining fondant black. For brim, use 9 in. fondant roller with purple guide rings to roll out black fondant 1/8 in. thick. Use largest round Cut-Out to cut circle for brim. Use a knife to cut a circle, 1 1/4 in. dia., in center for head opening.
Use fingers to shape remaining black fondant into a mound, 1 5/8 in. long x 1 1/4 in. wide x 1 1/8 in. high, for top of hat. Use your thumb to indent bottom slightly to conform to head shape. Use end of brush to indent mound for top crease. Use damp brush to attach top of hat to brim. Pinch front side of hat to indent and shape hat.
For hatband, use 9 in. fondant roller with pink guide rings to roll out white fondant 1/16 in. thick. Use fondant trimmer to cut a strip, 1/4 in. wide x 5 1/2 in. long. Use damp brush to attach strip to hat.