Robot has strange item of headgear (8)
I believe the answer is:
tarboosh
'item of headgear' is the definition.
'tarboosh' can be an answer for 'headgear' (tarboosh is a kind of headgear). I am not sure about the 'item of' bit.
'robot has strange' is the wordplay.
'strange' indicates anagramming the letters.
'robot'+'has'='robothas'
'robothas' anagrammed gives 'TARBOOSH'.
Can you help me to learn more?
(Other definitions for tarboosh that I've seen before include "Fez-like hat" , "Fez" , "Fez-like cap" , "top gear" .)