Pairing a long sleeve shirt with white and navy chinos is a great option for a relaxed ensemble. Not sure how to finish off this look? Rock black leather casual boots to step up the style factor. During the colder months, when practicality is imperative, it can be easy to surrender to a less-than-stylish outfit in the name of functionality. However, this outfit is a shining example that you totally can stay comfortable and remain equally stylish in the colder months. When it comes to outfit ideas for over-40 men, this look looks nice on most men.