Marrying an olive sweatshirt with cargo pants is a smart option for a casual and cool look. And if you wish to easily amp up your outfit with shoes, why not complement this look with a pair of dark brown leather casual boots? Seeing as it is getting colder with each day, this getup appears a viable option for the transitional season. Sartorial inspo like this will help you stay incredibly fashionable at 40 and beyond.