If you're on a mission for a laid-back and at the same time dapper outfit, dress in a dark brown crew-neck sweater and a long sleeve shirt. A pair of black suede chelsea boots easily lifts up any ensemble. With an ensemble like this in your winter closet, you're guaranteed to stay toasty and look stylish despite the nasty weather. This combo should encourage anyone who had doubts about classier style in his 20s.