Rock a blazer with a sweater vest for truly sharp style. For a more laid-back finish, why not add black leather desert boots to the equation? During the winter months, when warmth is key, it can be easy to settle for a less-than-stylish ensemble. However, this ensemble is a good illustration that you totally can stay toasty and remain equally stylish during the winter months. Wondering what you should wear as you slip into your 50s? This combination is the perfect answer.