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In advance: Make cookies. Tint dough desired skin tone. Roll out and cut 5 gingerbread boy cookies; and 10 triangle easel backs, 2 x 1 1/4 in., bake and cool.
Decorate with royal icing: Use tip 2 to outline and pipe in clothes; smooth with finger dipped in cornstarch. Add tip 2 outline and pull-out hair. Pipe tip 1 dot and outline facial features and clothing details. Attach flags to hands with icing. Let dry overnight. Attach easel backs to backs of legs with royal icing. Let dry.
Bake and cool cupcakes. Ice smooth in buttercream. Insert foil pix. Position cupcakes on stand and cookies around stand.
* Combine Brown with Christmas Red for brown shown.