Panama Hat

 This particular Fedora due to its lightness both in weight and colour plus open its weave should be more accurately called a Panama Hat. 

This particular Panama is made of hessian I think and probably stiffened with some sort of starch paste or glue but since purchased second hand and not detailed on any sort of label its really a guess

The loose weave and holes in the crown and make this a cooling hat for humid summers, designed to protect against the sun rather than other elements such as rain or wind.

The original Panama hats date back as far as 16th Century and originate in Ecuador where they were made from plated palm leaves. The traditional Ecuadorian toquilla hat is protected by its heritage status.

Never made in Panama the hat gots name mainly due to president Theodore Roosevelt's wearing one on his trip to oversee the construction of the Panama Canal. 

Purchase for £8 including carriage off an auction site called clutter buys.

Headscarf

 The headscarf is not traditionally a head-covering worn by men

Whilst a headscarf is not traditional, the same piece of fabric can be turned into turbans, shemagh and bandanas which are styles of head coverings worn by men. 

Maybe the only difference between a headscarf worn by women or men is the name, maybe the fabric might be more patterned for women, the knots different, but gender stereotypes are gradually disappearing, so worn today it does not really matter.

I think it looks smart, would certainly make use of it as emergency sun protection.

Bycocket Shaped Hat

This hat is shaped like a bycocket or robin hood hat, made of patterned fabric, lined and decorated with a button and feathers.

The hat is made of soft fabric which makes it sit very differently on the head, it flattens out spreading outside the circumference of your head. Without that stiffness or a band to grip the head, it also feels more insecure than it should.

This is one of those awkward hats which I'm not sure where I will use it, it's not general-purpose to go about walking in, does not fit in a fantasy or historical use, not silly enough to be a novelty hat.

Currently thinking it may get used for some sort of drippy nobleman character

This was a Christmas present, much appreciated even if unsure of use yet.

Reversible hat

The fabric hat is reversible so you can a brown or red hat 

I would hazard a guess that the hat is a medieval style, the kind that would normally be made from wool.

The hat is basically a square bag, that follows the shape of the head when worn and leaving 4 corners at the crown where there is an air pocket above your head.

Many shapes of historical hats do not have names, you could call it a beanie of shorts

I would say this hat suitable for any period from at least the 13th to 18th century. 

Mob Hat

 A Mob hat or cap was worn by Georgian women of any status. 

Its also called a Mop cap which is probably due to a subtle change its use from a frilly bonnet to a hat used by victorian maids who mopped the floor.

This style of hat is mainly associated today with Victorian maids and would normally be white.

Basically, a round cloth gathered with a ribbon or string to give a ruffle brim and covering.

Designed to keep the hair under control, modern plastic and net variants are used in clean environments such as food factories for the same reason.

These caps or a version of them were worn by men at least in the early 18th century but were predominantly women headwear.

Gold Fascinator

This hat was described as a Theatrical, Wedding, Gold, Empress Style. Medieval Reenactment Hat, Fascinator.

Fascinators usually are something associated with women's headwear rather than men's and are basically a hat that covers only a small portion of the top of the head and purely ornamental in function.

While possible designed for a woman, I can see easily being worn by a man

This fascinator is made of lightweight wire gauze, with trimming  

It could be used for an Arabian or East Asian Princess or Prince

 

Cheap Chinese Style Hat

 This hat is about as cheap as they come and even as a novelty hat not recommended

Mimicking some other watermelon style oriental hats, this is made of some cheap fabric over some thin foam, that both makes it uncomfortable and a poor fit. The shiny fabric is slippery and this makes it readily just fall off your head, no matter how tight you pull it down

I have a similar hat here and although also a novelty hat far more comfortable and better made

Tudor Flat Cap

 The hat further down is the last of a set of Tudor theatrical hats purchased as a job lot off eBay

Like the others, the label inside says RCA which I believe is the Royal College of Arts

A theatrical version of a cowpat hat or Tudor flat cap

Brown and cream, ideal for any Tudor play if any good plays from the period still exist.