I drew this concept drawing just now of my character Josh in a slightly different style to normal and personally prefer it to the way he looked previously - he's supposed to be in his late teens and I find he looks more mature in this than he did previously, and also think I can give him better emotions and draw him from more angles in this style. I just wanted other people's honest thoughts so I know whether or not I should go ahead with this redesign? If so then I'll likely update the appearance of Angus slightly too.
I would suggest refining the lines of his clothes, however. I can see you're going for baggy clothes, but you can convey that just as well with lesser amount of bumps, and make them less uniform. Baggy clothes bunch up in spots! Especially around joints, like the elbows and wrists, the knees and ankles.
He was initially 13, and I aged him up to 16 a couple of years ago. The only ways I really changed his appearance was by making him taller and giving him some upper lip hair but I still found it a little unrealistic for him to be in his late teens and still facially look (otherwise) like he was in his early teens.