For an outfit that offers functionality and dapperness, try pairing a navy long sleeve shirt with jeans. Let your styling sensibilities truly shine by rounding off this outfit with a pair of brown leather casual boots. During winter, when functionality is prized, it can be easy to settle for a less-than-stylish outfit. But this outfit is a stark illustration that you can actually stay snug and remain stylish during winter. So if you need outfit inspo for dressing as you pass the big five-oh, this outfit is perfect.