For rugged refinement with a twist, you can easily dress in a white and navy dress shirt and charcoal dress pants. Bump up your whole ensemble by finishing off with a pair of chelsea boots. In the colder months, when warmth is top priority, it can be easy to surrender to a less-than-stylish getup in the name of functionality. However, this getup is a striking illustration that you totally can stay warm and remain equally stylish during the colder months. And if we're talking style tips for 50-something guys, this look looks great on most gents.