This combo of a long sleeve shirt and navy jeans is proof that a pared down casual ensemble can still look really interesting. You can get a little creative on the shoe front and introduce tobacco derby shoes to the mix. During the colder months, when warmth is crucial, it can be easy to surrender to a less-than-stylish look in the name of practicality. But this look is a shining example that you can actually stay comfy and remain stylish at the same time in the colder months. Rest assured this ensemble is something you can totally wear as a gentleman over 40.