Sharp yet practical, this outfit combines a light blue long sleeve shirt and charcoal chinos. Give an elegant twist to an otherwise mostly dressed-down look by sporting brown leather casual boots. During winter, when functionality is everything, it can be easy to surrender to a less-than-stylish getup. This getup, however, is hard proof that you totally can stay snug and remain equally stylish during winter. As a 30-something Millennial gent, you probably want to start dressing more professionally. If that's the case, ensembles like this are a goofproof option.