Naomi is my deepest character, and as such, she's undergone the most changes.
Naomi was no different from stereotypical fantasy elves in 2011. As my worldbuilding wasn't settled, she was a half-nymph, half-human, and I've since grown annoyed with 90% of half-races in fantasy.
It was this picture of a young, tanned Naomi that prompted me to darken nymphs' skin and pull their ears down into a more anime-like style. It took awhile, though.
In my last days of high school, I dipped further into realism with Naomi than any other character. These sketches fueled my new-found love for semi-realism. Naomi was a dark heroine to begin with, but at this point she was practically evil.
These two doodles were the last I did of Naomi's initial design.
To this day, this image is the best representation of Naomi's story and design I have despite its anatomical errors. Naomi's story my only true tragedy (traditional definition: story in which the character makes the wrong choice) and the consequences for Naomi's actions are more costly than in any of my stories.
CURRENTLY: Naomi is a dark heroine still, but I've learned stuff. I removed most of her uncertainty, therefore increasing likability. She's no longer objectively evil and her design is significantly more unique than it used to be. She's my only character whose physical strength actually plummets as the story moves forward as her injuries pile up in a world without magic healing.