This combo of a dark brown leather military jacket and navy ripped jeans offers comfort and confidence and helps you keep it low-key yet contemporary. And if you wish to easily perk up this outfit with shoes, why not add a pair of dark brown leather casual boots to the mix? Seeing as it is getting chillier every day, this outfit appears a nice option for the transitional season. All in all, a perfect demonstration of laid-back style for 30-something Millennial men.