Probably not the way he looked, seeing as he implies he'd embraced the conman's lifestyle at the age of twelve. . . But I'll bet this is definitely the way Nick felt at 16 (or, if nothing else, the way all the musicians he was listening to at that age dressed).

I agree. Think this might reflect how he felt on the inside. But some nagging thought in his mind kept from going too far in the aggressive overtly stance thinking of his mother. So instead, he adopted the "Smooth Operator" approach, in which given what we see in the movie is a soft sell con, versus the "Godfather Machismo" of Mr. Big.

Also, like you said, Terastas, his taste in music (esp. given his Official playlist on Spotify) is how he lets out his more overtly rebellious emotions.

For some reason, just imagining him being a mommy's boy, none the less. I dunno, just think it's cute. x'3