Penitent, insincere and damaged, going topless (10)
I believe the answer is:
shamefaced
'topless' is the definition.
Both the definition and answer are adjectives. Maybe you can see an association between them that I can't see?
I don't understand how the remainder of the clue works.
Can you help me to learn more?
(Other definitions for shamefaced that I've seen before include "Looking guilty" , "became conscience-stricken" , "Very modest, bashful" , "Sheepish" , "Sorry-looking" .)