Want to infuse your closet with some laid-back menswear style? Choose a white and red crew-neck t-shirt and olive cargo pants. Add a dressier twist to this look by slipping into a pair of casual boots. During the winter season, when functionality is a must, it can be easy to settle for a less-than-stylish ensemble. However, this ensemble is a stark illustration that you can actually stay comfortable and remain stylish in the winter season. Those who are curious how to dress fashionably in your 50s, you have your answer.