For an outfit that's truly GQ-worthy, marry a beige blazer with olive chinos. Desert boots integrate smoothly within a myriad of outfits. In the colder months, when warmth is top priority, it can be easy to settle for a less-than-stylish look. However, this look is a striking example that you totally can stay cozy and remain equally stylish during the colder months. Guys who wonder how to dress stylishly in your fifties, you have your answer.