Like the convicts' old clothes? (8)
I believe the answer is:
timeworn
'like the convicts' old clothes?' is the definition.
I can't judge whether this definition defines the answer.
'like the convicts' old' is the wordplay.
'like the convicts'' becomes 'time' (I can't justify this - if you can you should give a lot more credence to this answer).
'old' becomes 'worn' (associated in meaning).
'time'+'worn'='TIMEWORN'
Can you help me to learn more?
(Other definitions for timeworn that I've seen before include "Familiar through overuse" , "Tired" , "Out of date" , "Decayed by long use" , "Overfamiliar through overuse" .)