1 Canadian Military Cap and 2 Unknown items

A friend had some items in his house and asked if i can identify it i noticed the marking on the aviator hat but the other stamp on it is faded pretty good and the wooden box looks military for the way its designed but i have no idea what it is.  he gave me the canadian military cap as a gift or if i wanted to sell i can. what are the retail prices of these items

flight helmet is RAF pattern. Dont know if its wartime or not
Overseas cap looks WW2 era.
Box is a WW1 US ammo box. Its about $20-25 around here in that condition.
I have no idea what the hats are worth. Leather one is at least $100

Fins...