When the setting allows a laid-back look, you can wear a black long sleeve t-shirt and black chinos. Take a classic approach with shoes and introduce black leather chelsea boots to your look. Figuring out a pulled together combo can be a bit difficult at times on its own. Add extra cold temperatures into the equation, and the whole thing becomes all the more difficult. Luckily, this here is your wintry inspo. This ensemble proves that dressing stylishly as a 30-year-old gentleman is quite manageable.