Opt for a shearling jacket and a beige hoodie to achieve a cool and casual ensemble. Kick up the appeal of your outfit by rounding off with dark brown leather chelsea boots. During the winter season, when comfort is essential, it can be easy to settle for a less-than-stylish outfit in the name of functionality. But this outfit is a clear example that you totally can stay warm and remain stylish in the winter season. A great example for any man who wonders how to dress maturely as a 30-year-old guy.