Consider wearing a teal blazer and a white dress shirt to look like a true fashion expert. Balance this look with more laid-back shoes, such as these tan suede desert boots. In the colder months, when warmth is imperative, it can be easy to settle for a less-than-stylish ensemble. However, this ensemble is a practical illustration that you totally can stay warm and remain equally stylish during the colder months. Definitely a goofproof option if we're talking dressing ideas for men in their 50s.