Latex Skeleton Mask

There are other things you can wear on head besides hats such as hoods, wigs, crowns and one of the other things is masks

This latex mask I'm wearing is from the Ascendancy prop box

Latex masks can be half masks which leave the mouth uncovered, face masks just covering the eyes and forehead or like this one full head masks covering the whole face and head.
These full head masks are the worst to wear as they restrict breathing but the main problem is condensation from breathing and general sweat.

You get a little puddle of fluid in the chin of this mask after wearing it for half an hour.

Thracian Cap

Thracian cap. made of cow hide

The style or shape is that of phrygian cap, i.e. with a forward pointing top the crown, smurf hat style.

Thracian caps where made of skins with the fur still attached, and then the rest of leather is left to dangle down over the shoulders.

You will find the style of hat in many images of ancient Thracian warriors or Bulgarian area history.

Purchased from a reenactment fayre, although you could easily make this yourself for cost of bit leather its only got one crude seam.

Probably going to be used for some sort of fantasy goblin.

Village Yokel

A simple felt hat, misused and abused makes a idea hat for anyone that is not wanting a fashion statement.

Ideal for playing characters such as farmers, peasants or the village yokel.

If you want to look a little (very little) smarter turn the brim up

Novelty Witches

Novelty Witches Hat probably for a Halloween costume

Made of velvet its works in a way, but does not mirror any reality.

The original owner of the hat donated it after wearing once for lrp event where she played the part of witch, see photos below.

The witches hat itself while not historical true does have its roots in history of the period witches were burnt in England. 

One theory I read is the pointed hat represents a church steeple so witches where made to wear them in last ditch effort to redeem them in the eyes of god. 

Another the hats shape is to do with mummified witches from China which were found wearing felt cones on their head.

More likely its a follow on from the wizard hat which was to do with demonising of the Jews in the medieval period.

One thing is sure most of the look is pure Hollywood from films like the Wizard of Oz.