Wretched, dismal-looking (9)
I believe the answer is:
woebegone
I believe this clue is a double definition.
'wretched' is the first definition.
(thesaurus)
'dismal-looking' is the second definition.
(I've seen this before)
(Other definitions for woebegone that I've seen before include "Dismal-looking" , "dismal look" , "Miserable in appearance" , "Looking sad" , "Sad, miserable" .)