You'll be surprised at how easy it is to put together this sophisticated outfit. Just a dark brown overcoat and a light blue vertical striped dress shirt. If in doubt as to what to wear in the footwear department, add a pair of dark brown leather loafers to the equation. Rest assured, this combo will keep you comfortable as well as looking seriously stylish in this transitional weather. Interested in dressing tips for 50-year-old gentlemen? This pairing is pretty inspiring.