What Should He Wear? . . .

I like #2 and #4. 

#2 I like the waistcoat contrast in this one to throw off the overuse of blue, and even though it's still typically formal, his long hair worn down gives it an edgier look .

#4 This looks like the outfit of a musician or artist. It mixes things up from atypical formal wear and suits his career. You can tell by looking at him that he does something creative. 

My take on his outfits.

1. He looks like he's going to his own wedding.
2. Looks like an accountant ready to do your taxes.
3. Festive, is he going to some fancy after party later?
4. Nice, put together and age and event appropriate, I think it's a winner.

I like the last one. Sharp, but not too formal. He is still a kid and deserves to not have to take up too much adulting at this point.

I think that perhaps the second outfit, the 3 piece suit. He looks stylish in it, without the formalness of the first one. It seems to suit him best as a teen dressed for a special occasion.