Hey Kyle,
I agree with the others here who are recommending longer sleeves on your shirt and jacket and shorter pants legs. Having no break in my trousers is a non-negotiable for me though, it doesn't have to be for you.
I'm also at Columbia right now and would be happy to recommend a tailor on the uws. Don't listen to anyone telling you to dress or look any way other than the way you want. There are dozens of us!!