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.
Melt white Candy Melts candy according to package directions and insert sticks following recipe directions. Use primary and garden candy colors to tint portions of melted white candy light orange (for skin tone shown) and black. Dip cake pops in melted skin tone candy. Chill until firm in stand 10 to 15 minutes. Reserve remaining candy.
Decorate cake pops. Melt light cocoa Candy Melts candy according to package directions. Use melted light cocoa candy and cut parchment bag to pipe hair. Use melted black candy and cut parchment bag to pipe eyes. Use reserved melted candy and cut parchment bags to pipe skin tone nose and light cocoa mustache. Chill until firm in stand 3 to 5 minutes.
Assemble pop. Use melted black candy to attach hat to head. Let set in stand 3 to 5 minutes.
The roaring ?20s are very contemporary! This man about town fits right in, featuring a white fedora made from rolled fondant and a cake pop face that is dipped and decorated in Wilton Candy Melts candy.