This combo of a brown houndstooth overcoat and blue jeans is perfect when you need to look stylish but have zero time to pick out an outfit. Complete this getup with a pair of brown snow boots to infuse a touch of stylish casualness into your getup. During the winter months, when warmth is imperative, it can be easy to settle for a less-than-stylish ensemble in the name of practicality. This ensemble, however, is a vivid example that you can actually stay toasty and remain equally stylish in the winter months. If you're often not sure how to dress your age while looking fashionable, this ensemble is a good illustration.