Beyond stylish and functional, this laid-back combination of a long sleeve shirt and black jeans will provide you with variety. Get a bit experimental on the shoe front and spruce up your ensemble by rounding off with a pair of black chelsea boots. No doubt, a fail-safe option if we're talking dressing ideas for 50-year-old men.
This relaxed combo of a long sleeve shirt and black cargo pants is a safe option when you need to look cool but have no extra time to assemble an ensemble. Black chelsea boots are an effective way to bring an element of sophistication to your ensemble. This ensemble proves that dressing your age and looking stylish are not mutually exclusive things.