Something you wear because you've always worn it? (5)
I believe the answer is:
habit
'something you wear because' is the definition.
I can't judge whether this definition defines the answer.
'always worn it?' is the wordplay.
'always worn' becomes 'hab' (I am not sure about this - if you are sure you should give a lot more credence to this answer).
'hab'+'it'='HABIT'
'you've' is the link.
Can you help me to learn more?
(Other definitions for habit that I've seen before include "Riding garment" , "Acquired pattern of behaviour" , "Custom; clothing" , "Regular practice" , "Monk's robe or repetitive action" .)