What the fool, the silly chap, has on his head? (5,3)
I believe the answer is:
cloth cap
'what the fool the silly chap has on his head?' is the definition.
Although both the answer and definition are singular nouns, I cannot understand how they can define each other.
'silly chap has on his head?' is the wordplay.
'silly' indicates an anagram.
'has' indicates putting letters inside.
'on his head?' becomes 'clot' (I can't justify this - if you can you should believe this answer much more).
'chap' is an anagram of 'hcap'.
'hcap' placed around 'clot' is 'CLOTH CAP'.
Can you help me to learn more?
(Other definitions for cloth cap that I've seen before include "Stereotypical headgear for the working classes" , "Flat hat" , "Flat headgear" .)