As you can see, looking sharp doesn't take that much work. Choose a crew-neck t-shirt and grey dress pants and be sure you'll look incredibly stylish. Black suede loafers will add a strong and masculine feel to any getup. During the colder months, when warmth is the priority, it can be easy to surrender to a less-than-stylish outfit. But this outfit is a vivid example that you totally can stay cozy and remain stylish at the same time in the colder months. This outfit is the perfect answer to the question of what to wear as you reach your 40s.