Team a navy blazer with a white vertical striped dress shirt for a clean-cut sophisticated outfit. For shoes, stick to a more elegant route with dark brown suede loafers. In the colder months, when comfort is imperative, it can be easy to surrender to a less-than-stylish look in the name of functionality. But this look is a good illustration that you totally can stay comfortable and remain stylish in the colder months. This combo demonstrates how 30-something Millennial gentlemen slay in the fashion department.