Slim raw denim (APC, Naked and Famous)- don't spend more than $200. You'll spill beer, blood, and pen ink on them in school. Wait until you're a denim head to spend more.
Good, basic sneakers. Common Projects can get as cheap as $200- try a pair on somewhere and grab them on sale. Nobody pays retail. For almost anything.
Wings and Horns hoody. Tigerfleece or large loop are pretty comfortable.