You can look cool and relaxed without trying too hard in an olive crew-neck sweater and a long sleeve shirt. Go ahead and complete your outfit with black leather chelsea boots for a sense of sophistication. During the colder months, when functionality is above all, it can be easy to surrender to a less-than-stylish outfit. But this outfit is a stark illustration that you can actually stay comfortable and remain equally stylish during the colder months. This is a stylish yet age-appropriate ensemble for 30-something men.