How to Make a Little Orphan Annie Costume. When most people think of Little Orphan Annie, they imagine of a little curly redheaded girl singing "The Sun Will Come Out Tomorrow." Simply adding a few details to your outfit makes that little redheaded orphan costume easy to make. Below are two different versions of the costume: Annie as an orphan and Annie in the red dress.
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Annie as an orphan
Wear a curly red wig. Annie had short tight curly hair. If you already have red hair, you're one step ahead.
Apply dirt or makeup to your face and hands to make you look dirty.
Find a dingy button up dress to wear. Add stains and wrinkle it up before it's time to wear. Remember you want to look like an orphan.
Add an old apron and cardigan sweater.
Pull one of your socks up to your knee and leave to other down. Add old brown shoes or old lace up boots.
Place a broken locket around your neck as an added detail. You can also carry a pail with a rag in your hand since Little Orphan Annie did a lot of cleaning at the orphanage.
Add a shaggy dog adds to the costume to represent Sandy if possible.
Annie in her red dress
Wear a red curly wig.
Buy or sew a red collared dress that comes just above the knees. Add a white belt around the waist.
Add a heart-shaped locket around your neck. White socks or tights and black patent leather shoes go great with this costume.
Don't forget to add a shaggy dog by your side.