A blazer and navy chinos worn together are a match made in heaven for those who appreciate effortlessly sleek combinations. For something more on the dressier side to complete your outfit, finish with a pair of black leather derby shoes. In the winter months, when warmth is a must, it can be easy to surrender to a less-than-stylish look. But this look proves that you can actually stay comfy and remain equally stylish during the winter months. This getup demonstrates that even in your 50s your sartorial options are still pretty much limitless.