Tricky thing to wear? (3)
I believe the answer is:
hat
'wear?' is the definition.
(hatting is a kind of wearing)
I don't understand how the rest of the clue works.
Can you help me to learn more?
(Other definitions for hat that I've seen before include "Cap" , "Bowler maybe" , "Accessory" , "Headwear" , "Headgear decoration" .)