The "Little Orphan Annie" character was made popular first as a comic strip, and then by a theatrical musical production that launched on Broadway in New York in 1977. The storyline reveals how a child named Annie was left at an orphanage and was later adopted by a wealthy family. You can take a few different approaches to achieve an Annie costume. You can dress like the Annie character did when she was in the orphanage, or like she did after she left the orphanage.
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The Annie character had two main looks, one that was more formal and clean and the other a casual, ragged look. The character was often seen in a red dress with a white collar and a white sash around the waist, after she left the orphanage. To dress as Annie when she was still an orphan, you could wear worn and dingy overalls over a T-shirt or tank top, or a loosefitting, ragged dress.
The character's hair is red and curly. A curly, red wig will help you achieve this look. To dress as one of Annie's friends in the orphanage, create two braided pigtails on either side of your head, separated by a part down the middle.
Shoes and Socks
If you are aiming to achieve the "clean" Annie look, you could dress in black patent leather girl shoes with ruffled fold-down ankle socks. To dress as the ragged, orphan Annie, wear worn-out lace-up boots without socks, or with socks with holes in them.
People with red hair often have freckles. You could use a red or light brown make-up pencil to put freckles on your cheeks. A light layer of red or pink lipstick on your lips can help you achieve a youthful appearance. Use a brown make-up pencil to create a dirty face if you are striving to represent Annie in the orphanage.
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