Rock a grey long sleeve henley shirt with dark green chinos for a fuss-free outfit that's also put together nicely. You can take a classic approach with shoes and make brown suede desert boots your footwear choice. In winter, when functionality is a must, it can be easy to settle for a less-than-stylish ensemble in the name of practicality. But this ensemble is a bright example that you can actually stay warm and remain equally stylish in winter. A cool, less conservative combination for a young guy.