No More Mr. Nice Guy

I am not a fan of poking things into my eyes in the morning and then poking them out of my eyes at night.

I think glasses look good on you. For the hair I'd use some hairspray and push it up and back, sorry if that's hard to understand...
And girls in my college seem to really go for the woodcutter type of guy, they always complain about guys becoming too feminine (that doesn't mean they want smelly, unclean guys). So I'd just get a good set of T-Shirts and nice fitting pair of jeans and you're good to go. An effortless look. Also don't shave your beard, just trim it.