Carry On Up the Revolution

This is what called a Barge cap or Breton Cap  (Not to be confused with a Breton Hat which is a totally different hat shape)

Its also known as fiddler cap, Lenin cap, skipper cap, or mariner's cap, although that depends on if they have embroidery on the headband or peak.

Normally made of thick wool to provide the main stiffness, they are always peaked, they have firm wide headband, and usually come in black or navy blue.

Worn by 20th C merchant navy, barge owners and northern European factory workers.

The Fiddler cap name came about because of the film Fiddler on the Roof where the main character Topol wear one.

They came in to use in big way in Tsarists Russia due to the banning of Jewish style head ware.

Worn with with a black scarf it creates a ideal early 20th Century workers revolutionary look.

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Bucket Hat

A couple of laces make thus old bucket hat really useful in the wind.

Bucket hats probably started has practical fishemens hat in some oiled fabric, but were adopted has fashion hats in the 1960's.

Also known as session hat, fisherman's hat, or Irish country hat.

Photo above by Tom Garnett from Dark Colony Event

I've had this hat for a least 27 years as went with me to Thailand 1989 as can be seen in the photos below

My taste in clothing has got a little duller since this photo below with the very sun burnt legs to match the shorts.

I Just Need a Stormy Sea

This is what's known as Sou'wester 

A practical hat used by seaman for protection against rough wet weather, The brim is wide and slanted basically designed to stop rain running off it down the collar of your coat. 

A good chin strap also keeps it in place in high winds.

The name Sou'wester potentially comes from the South Westerly winds which brought rough seas, this may have some truth, but I can't find anything to back the claim up.

In some countries its just called a fisherman's cap, however they are not necessarily the same thing as as Sou'wester for example they are not needed to be fully waterproof.

Sou'wester are made of oilskin which can any be fabric made waterproof but is traditionally canvass covered in linseed oil or tar this one however is 100% PVC but works fine.