yeah it was probably a bad time to ask considering i'm at fashion school right now...um.
you guys are taking this all way too literally- there are ways to take those looks posted above and make them more appropriate for older guys. like said, staple pieces.
(and by the way, i have only once in my life ever dated someone who was actually the same age as me, so no, this is not what i want a 17 year old boy to look like).
if you take some of the dior homme looks i posted earlier and subtract the suspenders, hats, sunglasses and other accessories, you are left with a slim fitting polo and a slim fitting pair of pants. this look is ageless, timeless, and crisp. now add your choice of shoes (my personal favorites being of course your oldest pair of chucks), and you have a solid outfit.
polos are not my personal favorite item of menswear, but they can be a very nice wardrobe staple and they can work quite well depending on the context.