For a laid-back and cool outfit, reach for a grey windbreaker and jeans — these two items play perfectly well together. On the fence about how to finish? Add white and blue athletic shoes to this outfit for a more laid-back touch. When it's one of those gloomy fall afternoons, what better to cheer it up than a dapper ensemble like this one? This outfit is a great inspiration to anyone who had doubts about sporting casual outfits as a 40-something man.