For a fail-safe smart option, you can never go wrong with this pairing of an overcoat and a long sleeve t-shirt. And it's a wonder what brown athletic shoes can do for the look. And if we're talking casual clothing for 50-year-old guys, this ensemble is ideal.
For an outfit that's nothing less than gasp-worthy, dress in an overcoat and a long sleeve t-shirt. Introduce a pair of black leather casual boots to your look et voila, this getup is complete. A good combo to make you a well-dressed man over 50, rather than just a man over 50.