For something on the casual side, reach for a sweatshirt and a crew-neck t-shirt. Infuse a fun feel into this ensemble by rounding off with a pair of yellow leather high top sneakers. During the colder months, when warmth is key, it can be easy to surrender to a less-than-stylish ensemble in the name of practicality. However, this ensemble is a practical illustration that you totally can stay toasty and remain equally stylish during the colder months. This outfit demonstrates that as a middle-aged man, you still have a vast array of dressing options.