Stop motion web series The Most Popular Girls in School features a character with headgear. She started out as an extra in episode five, but quickly became a prominent supporting character. Also, the series is excellent, with great writing and performances.

https://dereferer.me/?https://www.youtube.com/watch?v=YRM0zoB6LvM episode five
https://dereferer.me/?https://www.youtube.com/watch?v=-STtD96doeo episode one

Don't worry, the sound and animation quality vastly improves.