As you can see here, it doesn't take that much effort for a man to look seriously stylish. Just try pairing an olive blazer with blue jeans and be sure you'll look incredibly stylish. Our favorite of a countless number of ways to finish off this ensemble is with a pair of tan suede desert boots. A wonderful example of comfortable style, this outfit must be in your collection when winter weather settles in. Interested in fashion for gentlemen in their fifties? This getup is pretty inspiring.