I never brought realism up haha even if it is cartoonish you still have to stick to proportions and how it works, naruto is anime not live action but they still go for realism and how things work.

Deleted last post since it was pretty useless.

Here is the newest (and possibly the last) image.

Work with shadow bud, the head is still round so delete that and add more hair and a lot of shadow to signify that he is under a hoodie.