A hoodie and black and white chinos matched together are a perfect match. Rounding off with a pair of grey athletic shoes is the most effective way to add a carefree vibe to your getup. When you have one of those dreary autumn days, sometimes only a kick-ass ensemble like this one can get you out the door in the morning. And if we're talking casual outfit ideas for gentlemen in their fifties, this ensemble looks great on most gents.