Help me cloth him, without him looking all tacky.
Han Solo style
It's not a clothing challenge unfortunately, I'm literally having a hard time choosing the proper clothing for him.
What could help is if you give us some information about his character.
I didn´t think it was a clothing challenge
Six year from a middle class family, with loving parents, US citizen, Tire 2 city resident, bit mature then his peers, slight womanizer.
I feel like your description is still very vague. But I also feel like 90% of boy fashion is just a t-shirt with pants.
(Ignore the colors at bottom)
This is what came to mind after reading your description. Hope you like.