being in high school, you'll probably stick with tees, polos, button-downs, and sweaters (and jeans, of course).
colors and patterns aside, i think your overall fit could use improvement. you could probably drop a size in both...
you're probably looking at some type of boot. the standard answers you'll receive are:
clarks desert boots
red wing gentleman travelers
alden indy boots
the first i wouldn't recommend since winter is here (unless...