Clothing

• 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 loose-fitting, ragged dress.
  
  

Hair

• 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.
  
  

Makeup

• People with red hair often have freckles. You could use a red or light brown makeup 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 makeup pencil to create a dirty face if you are striving to represent Annie in the orphanage.