If you're on a mission for a street style but also dapper outfit, wear a navy denim shirt and blue skinny jeans. Complete your outfit with brown suede casual boots for an extra dose of class. In the winter months, when warmth is everything, it can be easy to settle for a less-than-stylish outfit in the name of functionality. However, this outfit is a practical illustration that you can actually stay snug and remain stylish at the same time during the winter months. Laid-back combos for 30-something gentlemen aren't actually that hard, as you can see here.