Ignoring all the dating-and-relationships-at-16 drivel here's my 2 cents: First, don't spend too much money on this stuff. I had a nice collection of well fitting selvage denim until I started cycling at 18 and then hit another small growth spurt at 20. Don't make that mistake. Second, unless you're required a jacket and tie for school why not focus on some basics with good fit? Dark denim, some chinos on the bottom with polos, sweaters, and oxfords. Ditch the Nikes or whatever (doesn't appear that you'd be wearing sneakers anyway) and go with some chukkas or plain toe oxfords. Basics and good fit will go a long way, and (not sure what the status quo is in NZ) I'd wager you'll look better than most. Unless of course you're going for the Harry Potter/Curt from Glee (on a tame episode) look. If so, go for it. Too much time spent on these forums can really warp perspective.