Shoes for casual clothing

Most of the time I wear jeans, khakis, and cords with a polo untucked. In winter I wear sweaters and then tuck my shirt in so the shirt is not visible below the sweater. I was wondering, what sort of shoes would go well with this type of dress? I was thinking along the lines of some suede chukkas, but other than that I cannot come up with anything else. I'm not sure if it matters that my polos are untucked or not.

Also, I am trying to keep cost around $300 if possible.

Thanks