If you use the old way to import items(with item test) you can create a zip folder containing all the hat for each class, with new import method unfortunaly i can't say, cause i didn't use it.

This is a work in progress for a item that i want to submit. I would like to know what do you think about it, critcs and improvment!

https://drive.google.com/file/d/0B4mo1a-BK_riaWtNZDlnMjZRS00/edit?usp=sharing

Thanks in advance!