A crew-neck sweater and a white and blue dress shirt are essential in a functional casual wardrobe. For something more on the classy side to finish off your ensemble, throw a pair of black leather ankle boots in the mix. In the colder months, when warmth is the priority, it can be easy to settle for a less-than-stylish look. But this look is a stark illustration that you totally can stay toasty and remain chic at the same time in the colder months.