You'll be surprised at how easy it is for any gentleman to get dressed like this. Just a black overcoat paired with black chinos. To infuse a carefree feel into your outfit, complement this look with a pair of grey canvas low top sneakers. In the winter season, when warmth is the priority, it can be easy to surrender to a less-than-stylish look in the name of functionality. However, this look is a stark illustration that you totally can stay cozy and remain stylish in the winter season. As a gent in his fifties, you'll love this getup.