Do I look dumb?

I like the fits that don't involve polo shirts, I think polo shirts + not peak fitness = moobs for the most part. Keep looking around the forum, look at the WAWYTs, the ask question threads, and the I have a jean thread.

yes, but you're 16 so nobody will care

^ true.

Well yes, you do look dumb. I guess since no one else is helping you, check out the WAYWT thread to find out how something should fit. Learn what fits you before burning all your money on mall brands.

Nah dude you look fine. The fit on the shirts and shorts looked perfectly acceptable to me. Polo shirts will never really fit perfectly (that is, if you don't spend $200+ on them), so just get ones that fit you in the shoulders and chest. A little bagginess is to be expected, but I've found Lacoste brand is cut slimmer in the waist than most others.

That being said, when I was your age (not too long ago really) I started to wear button-downs almost all the time. Buy ones with your correct neck and arm measurements and then take them to a competent tailor to have them tapered in the sleeves and body. There is no avoiding this if you want to look better than the vast majority of your peers, so just accept the delayed gratification of buying a shirt only to wash it once and then send it straight to the tailor as part of your life. Get some nice belts, tuck in the shirt, and roll up your sleeves. This is the precious middle-ground in high school of distinguishing yourself as well-dressed while not being considered a douche.

Boat shoes and penny loafers are perfect. Fresh kicks too.

EDIT: Orange polo is definitely too big. Short sleeve button-down is the best fit.

You are incorrect.

As I'm sure you've noticed by now, everyone on this board seems to have a huge chip on their shoulder, and usually aren't friendly or helpful at all. If you're looking for quality clothing advice I suggest you go to: http://boards.4chan.org/fa/

It looks fine man. It's kind of the preppy looking. It is also a classic look. I'm in college and still dress that way. Just no cargo shorts or affliction shirts.

Perhaps some of your shirts could fit a bit better but you're still in the growing phase, so what might fit today might not fit tomorrow, and vice-versa.

People are far too busy thinking about themselves to give your appearance more than a cursory glance. You're on an average person's radar for about 1-2 seconds, then they're back to the chatter in their heads. So don't sweat it, because nobody is giving you much thought.

Great advice, definitely.