doleful

ˈdəʊlfʊl
ˈdəʊlf(ə)l

adjective

expressing sorrow; mournful.

a doleful look

mournful,woeful,sorrowful,sad,unhappy,depressed,dismal,gloomy,morose,melancholy,miserable,forlorn,wretched,woebegone,despondent,dejected,disconsolate,downcast,crestfallen,downhearted,heartbroken,heavy-hearted,despairing,desolate,grief-stricken,tearful,teary,lachrymose,blue,down,down in the mouth,down in the dumps,weepy,dolorous,heartsick,heartsore