Ushanka

Ushanka comes from a Russian word meaning ears.

This fur-lined cap comes with fold-down ear flaps that can be tied up to the crown of the cap, or fastened under the chin to protect the ears lower face from the cold. 

The Ushanka cap or hat is winter wear worn any from the USA to Russia but is very popular with Soviet naval officers

Traditionally made from rabbit or sheepskin and used in all sorts of extreme cold climates

This could also be called a trapper hat, but a trapper hat is not necessarily fur lined or designed for extreme cold.

This hat is a tourist variety with cheap soviet style badge and artificial fur but is still a practical hat that not just novelty wear.

Side Cap

A side cap is a fold-able military cap with straight sides, no brim and hollow crown which when worn forms a very distinctive shape.

In the UK its officially known as field service cap, in the US its called a garrison cap or flight cap.

The best feature of this cap is can easily be folded into a pocket, over the belt or under the shoulder strap of a military uniform. 

This cap sports a Russian badge so probably from a Russian unit but since I found it at cat boot I no idea for sure.

Serious Russian

This trapper style hat did start its life with a hammer and sickle badge on the front and was advertised as a Russian Army Style Winter Hat, which is what it is.

Made of fake fur which covers the outer surface, its built around a trapper style hat design with ear flaps and ties for under the chin, that are ideal for what I imagine Russian winters are like

This Russian can be fun.

Perhaps he can't ear well with flaps down.

 But is quickly serious again in to keep up his appearance.