Since school has a dress code I unfortunately have to comply with that. Right now its a polo shirt and fancy shorts. For some strange reason they don't limit the shoes, so I wear basketball shoes because that completely matches. Over the winter/fall though the dress code is more strict. Dress shirt, tie, and dress pants. Once again, they don't limit shoes and once again, basketball shoes match completely with the rest of the stuff.
Casually I'll wear a t-shirt and cargo/athletic shorts with the same shoes mentioned above. When its cold I wear a hoodie, jeans, and the same shoes.
Whatever's at the top of my drawer. Usually sweatpants and hoodie in the winter (no coats, I DESPISE coats), and in the summer, I wear basketball shorts (Even though I don't play basketball) and a random t-shirt from my huge pile.