Make a dark brown leather bomber jacket and beige chinos your outfit choice to put together a razor-sharp and current relaxed casual outfit. Feeling transgressive today? Change up your outfit by finishing off with white and navy canvas low top sneakers. When leaves change color and fall starts to take over, you'll love this combination as your go-to for transitional weather. When it comes to casual clothing for 50-year-old gentlemen, this combo is perfect.