I think it would look great with a certain look i.e. White top plain or textured (off-white or cream would work too I guess), black bottom, some white or beige shoes, and if you want a white beanie or similar color hat wear
Is that a III? It must be. I'd recommend sizing up one but that's probably only because I know what it is and how SS styled it. Nothing wrong with the fit really, if you leave it hanging. Don't button it.