People are definitely going to ask why you're all dressed up, and assume you were at work or something.
OCBD are actually very easy to incorporate into regular wear, provided you have the appropriate cut of a shirt. I usually wear mine with non-indigo jeans, shorts, and certain chinos. The thing with chinos and jeans are that some cuts will ultimately look more office dress than others. The cut of pants can really determine whether you have a streetwear look, a casual look, or a business look. Try looking at slimmer pants to kind of 'tone down' the perceived formality of the OCBD. The OCBD is actually one of the most versatile pieces of clothing in my opinion.
+1 on the above.
What does the average Northern U student dress like? I think that the average state of dress is something to be considered, as each school has their own style.
Having said that, I think OCBD are perfect shirts for the college male. OCBD and polos can easily be the backbone of a college wardrobe. That and fun t-shirts (odds are you won't wear these nearly as much once you leave college, so enjoy it while it lasts).
I would avoid slacks, dress shoes, and anything else that is business or business casual. Not to diverge into life advice, but you really do not want to be that one person who shows up to parties looking like he came from work on wall st. And we can all be honest, there was "that guy" at each and every one of our schools. You're in college. I would say think preppy rather than business if you really want to up your dress in undergrad; think preppy student rather than a Fitzgerald cut suit at Brooks Brothers.
For shoes, I would stick with boat shoes, Rainbows, and suede/canvas loafers or mocs. Dress shoes in a non-business setting are hard to pull off, unless you're a trend setter type IMO. The closest thing I have to a dress shoe for casual occasions are suede oxfords, which means not even close to dress shoes. Even JFK wears Converse All-Stars when he is throwing a football around.
My top advice would be to figure out the whole slim/tailored fit thing. A well fitted anything (be it casual/preppy/business) will be head and shoulders above trying up a wardrobe just for the sake of going dressier.