Reviewing the Situation

This crumpled top hat makes a perfect hat for a late Victorian tramp.

or a Fagin like villain.

This well-battered grey top hat look takes time or skill to produce, or just luck but is perfect for theatre or larp.

Anyway, I now need to pick a pocket or two.

Hooded Shirt

I can't see what practical purpose having a hood on your shirt offers, at most perhaps a bit of a sunshade.

So it's fashion, well you can be a judge of if this is a good look.

This shirt is handmade in Nepal using properly paid real 100% people.
(no people were harmed making this shirt, some may be harmed by looking at it)

Too young to be an original hippy and too old to be a new hippy, still a comfortable summer shirt that will get you noticed, if you want to be.

Hooded Cloak

A Cloak has been around since the times ancient Greeks and Romans and probably before that. 

It's a garment to wear over your normal garments that is easily added and removed as needed for weather protection, whether that be sun, rain, wind or cold.

They come in many varieties, some with hoods, some without, some down to ankles or some finishing just below at the knee, (any shorter and they become Capes)  they can be ornate, trimmed with fur or anything, they can ceremonial, give you invisibility, worn to the Opera but are usually just practical. They are usually lined, they don't have arms but may have slits for the arms to pass through. 

The only common thing is they fasten at the front at the neckline with a buckle, button, chain, broach or indeed any fastening that can hold the weight of the fabric on its own as its the only fastening.

This is a fantasy hooded cloak 

Pakol

This hat is called a Pakol also known as a Chitrali Cap

It is a soft round flat-topped hat, usually made of wool and typically come in light natura colours such as brown, walnut, cream, ivory, grey

The Pakol originated in the Afganistan/Pakistan region and was made famous by the Mujahideen.

This hat is also the same shape and construction as the ancient Macedonian Kausia hat, worn by men in ancient Southeast Europe.

I read that before it is put on this hat resembles a bag with a round with a flat bottom. You then rolls up the sides nearly to the top, forming a thick band, which then rests on the forehead.

This hat has the band sewn up so I can't show this.

Chilly Weather Hat

This Hat is called a Chullo.

Traditional to the people of the Andean mountain range of South America which stretches from Venezuela in the north right down to Chile in the south, this style of hat is more than a thousand-year
 old.

Usually made from alpaca, llama or sheep's wool

Alpaca wool like the one I'm wearing is particular good at insulating the wearer from the harsh elements of the mountains.

This is a very soft hat, almost felt like, I have no idea if that is typical of Alpaca wool.

Chullos have ear flaps that can be tied under the chin to help keep you warm, they come in many colours, but like Scottish tartan, the colours are significant to certain peoples of the Andes.