I think grey flannels in any shade would be great. Dark green moleskins maybe too. For shirts, a solid blue OCBD would probably be ideal, but you might be able to make a university stripe or checkered tattersall work. Brown shoes in almost any shade would fit, and a brown oxford with lots of broguing would work, but I'd prob. go for a blucher, loafer, or chukka, as you mention. Your friend dopey would give you great feedback irl.