This pairing of a black shearling jacket and navy plaid chinos is a safe and very stylish bet. Does this ensemble feel all-too-classic? Invite brown suede low top sneakers to mix things up. During the winter season, when warmth is paramount, it can be easy to surrender to a less-than-stylish ensemble in the name of functionality. But this ensemble is a stark illustration that you totally can stay comfortable and remain equally stylish in the winter season.