Go for a simple yet stylish look putting together a black pea coat and chinos. If in doubt as to what to wear on the shoe front, go with dark brown leather casual boots. Planning a standout outfit can be challenging on its own. Enter cold temperatures into the equation, and the whole thing becomes even more difficult. No worries, this here is your winter inspo. A no-brainer for 30-something Millennial gentlemen in search of a more professional image.