I had something like that and found it hard to mix - went poorly with my white-ass skin.
Sorry for the delay. All of their shirts are phenomenal, and they have a sale now, so you can indeed get them for roughly $50 in store (just did so a few days ago). A made-to-measure alternative that gets phenomenal reviews is Luxire, but that might be too much. If you want made-to-measure and don't mind sacrificing quality a bit, Modern Tailor is tolerable.
But yeah, Brooks shirts are awesome and kinda hard to beat. I'd also explore Denim Dan's recommendation, though I've never had a Giltman shirt.
Preppy as fuck. Polos, t-shirts, stuff like that?
Ehh, it's a parka. Sure, why not.