A friend of mine asked me to design a dark reimagining of Dorothy from The Wizard of Oz, so I gave it a try. I read up on the source material, and Dorothy is described as having two loose braids and wears a blue and white gingham dress, so I stuck with those. In the original story she wears silver shoes, so I stayed with that as well.
I was thinking in this version her sword would be based on a bowie knife since it was the closest thing I could think of that could be a "classic american sword", and this sword would be Toto. I'll have to do some more design work in the future, I was going to draw the Scarecrow, Tin man, and Cowardly lion as decapitated heads she carries around.