Raggedy Ann and Andy
If you don't mind donning yarn for hair and have no problem literally painting your cheeks, this costume could be just what you've been looking for! Moms and daughters can sport matching Raggedy Ann outfits, complete with tights and Mary Janes. Or, consider dressing your son up as a sweet little Raggedy Andy, with rosy cheeks, a triangle nose and the requisite blue pants and bow-tie combo. If this costume option strikes your fancy, however, be sure to do it before your little man gets too old. Most moms would be hard-pressed to get any boy over the age of 3 to agree to this getup, regardless how much candy he'll receive.