Step up your off-duty style by opting for a blue denim jacket and a white long sleeve shirt. If you're hesitant about how to finish off, a pair of dark brown leather casual boots is a tested option. In the colder months, when comfort is paramount, it can be easy to surrender to a less-than-stylish getup. However, this getup is a stark illustration that you can actually stay cozy and remain stylish at the same time during the colder months. Those wondering how to dress fashionably as you get into your 40s, you have your answer.