Opt for a grey long sleeve shirt and navy jeans for a day-to-day look that's full of charisma and character. To give your outfit a more sophisticated aesthetic, complement this outfit with derby shoes. In the colder months, when practicality is key, it can be easy to surrender to a less-than-stylish ensemble in the name of convenience. But this ensemble is a practical illustration that you totally can stay comfortable and remain stylish at the same time in the colder months. As a man over 40, you're sure to appreciate this combo.