A big plus 1. A v-neck t-shirt would go a long way to dressing this up and making it look sharper. I really can't tell fit from the picture, but a well fitting shirt and pants can really elevate even the most basic of ensembles. I know it's warm in Chicago today, but a sweater can dress things up as well. You could also make this look sharp with a quilted jacket or a Barbour, which would coordinate well with the HIggins Mill.