Wear a navy overcoat with charcoal dress pants if you're aiming for a neat, sharp ensemble. You could perhaps get a little creative in the shoe department and complement your outfit with brown leather casual boots. During winter, when warmth is everything, it can be easy to surrender to a less-than-stylish ensemble in the name of practicality. But this ensemble is a clear example that you can actually stay toasty and remain stylish at the same time during winter. As a 30-something Millennial gent, you probably want to start dressing with more elegance. In this case, ensembles like this are perfect as inspiration.