For something on the classy end, consider wearing a blazer and a dress shirt. Let your outfit coordination sensibilities truly shine by complementing this outfit with grey suede ankle boots. In the colder months, when warmth is the priority, it can be easy to surrender to a less-than-stylish getup. However, this getup is a vivid example that you totally can stay comfortable and remain absolutely chic at the same time in the colder months.