To create a casual menswear style with an edgy spin, dress in a white and red crew-neck t-shirt and olive cargo pants. On the shoe front, go for something on the dressier end of the spectrum by rocking a pair of casual boots. Piecing together a kick-ass combination can be a bit challenging on its own. Add extra cold temperatures into the equation, and the whole thing becomes all the more difficult. Fear not, this here is your wintry inspo. This combo is the perfect answer to the question of what to wear as you slip into your 50s.