If he's an apprentice, maybe the first one's slightly goofy look could be attributed to the awkwardness of youth? Or maybe the second one is just how he sees himself, and others might not see it in such a dramatic light? You could easily work both of those into his personality too, if you wanted. Might be interesting to see how his opinion of himself and the reality of his actions differ--for instance, if he sees himself as the badass second pic, but his actual skills aren't up to his self-image so he ends up biting off more than he can chew. 

Damar's too inquisitive and reliant on his own former Master at this point to take an apprentice of his own, though, sorry.