Design-wise, the 90s outfit can't be beat. It tied the perfect bow on that charming little punk personality of his. As far as being used now though, I think it's overstaying its welcome. Even with the little updates its gotten, I just can't help but feel like there's no reason for this young man to keep wearing what he did as a 15 year old "newborn". Give him a new fit!
I used to hate the black tee because I saw it as toning him down unrealistically (maturing teens don't just completely eliminate their senses of style LOL), but I've since grown fond of it. Still tired of it too, though.