What do you call this kind of t-shirt?
if you want to be menswear, sure. make sure the color of each piece complement each other and don't look out of place, the jeans fit well (tapered), and a nice button up. If it's cold where you live, try chambray.
I like the look of Red Wing's "Classic Oxford", but I'm not exactly ready to spend $250 on shoes. What are some cheaper, decently tough shoes in the same style for <$150?
Thinking of copping brown shoes that will go well with navy suits, just wondering, are all of them fine if paired with navy jeans as well? Or is there a specific type of shoe that looks fine if worn formally but not with jeans?