As an artist she has to blaze her own path and doesn't care what everyone else is doing. She wants to be the best at whatever she is doing and usually is but when it comes to clothes the more free from trends the better. New or used it doesn't matter, versatility is a plus and color schemes are in the eye of the beholder.
With no parents around the only ones to impress are his teachers and impress he does. Excelling at every subject in school he tutors the other kids who struggle. Favorite activities include computer languages and anything that can potentially lead to a house fire. Which fits the edgy, rebel image he hopes to project, despite being on honor roll.
"Eh?" If that is your reaction to what he's wearing his day has been made. If you get it, that's good too, but he really likes it when you're confounded. Maybe it's the joy of informing you. He has to keep up with the other smarty pants in his group so this is how he stands out. Not in an academic way but in a clever, made you look kind of way. The more obscure the message the better.