What does a guy do for a dressy-looking, casual shoe? He certainly can't wear wing tips, and loafers are passe.

A lot of guys have trouble with shoes because they tend to make them an afterthought. You're right, you cannot wear your dress shoes with your more casual outfit. Several versions of lace-up shoes with Vibram soles, made in soft-finished leathers, such as calf suede or deer, look great with brushed cotton, corduroy or even flannel trousers. Loafers are not necessarily passe. When loafers are made in softer leathers and paired with casual soles, you get a modern, relaxed look. A stiff, tasseled loafer is not right for a sportier look.