For a casually smart getup, dress in a black overcoat and black chinos — these two pieces fit nicely together. Get a bit experimental on the shoe front and play down your ensemble with a pair of beige suede desert boots. During the colder months, when practicality is everything, it can be easy to settle for a less-than-stylish ensemble in the name of practicality. But this ensemble is a stark illustration that you can actually stay cozy and remain equally stylish in the colder months. So if you're searching for a good-looking yet age-appropriate combination, this one fits the task well.