Why not team a crew-neck t-shirt with olive cargo pants? As well as super comfortable, these two items look amazing combined together. Our favorite of an infinite number of ways to finish this look is with grey athletic shoes. As you can see here, it's extremely easy to look on-trend and stay comfy when colder weather arrives, all thanks to outfits like this. This combination should encourage anyone who was doubtful about sporting casual outfits as a middle-aged man.