Consider wearing a white dress shirt and charcoal jeans for a proper elegant look. A pair of dark brown leather casual boots makes this ensemble whole. In the colder months, when comfort is paramount, it can be easy to settle for a less-than-stylish getup in the name of functionality. But this getup is a vivid example that you totally can stay toasty and remain stylish in the colder months. If you're wondering how you should dress as a 30-something Millennial guy, this pairing gives a good idea.