This pairing of an olive parka and blue jeans looks well-executed and makes any gent look infinitely cooler. Put an elegant spin on an otherwise all-too-common look by sporting a pair of chelsea boots. During the winter months, when warmth is crucial, it can be easy to settle for a less-than-stylish look in the name of convenience. But this look is a good illustration that you totally can stay comfortable and remain stylish at the same time in the winter months. As you see here, as a 50-something guy, you still have a wide array of styling options.