Such items as a navy harrington jacket and navy vertical striped chinos are an easy way to introduce understated dapperness into your daily casual lineup. If you're not sure how to round off, complement your look with white and black canvas low top sneakers. So if you're scouting for a cool winter-to-spring outfit, this just might be it. Think over-50 guys can't pull off cool casual outfits? This combo will prove you wrong.