Opt for a grey wool blazer and charcoal jeans if you're aiming for a sleek, seriously stylish outfit. If not sure about the footwear, go with a pair of brown leather casual boots. During the colder months, when warmth is key, it can be easy to settle for a less-than-stylish ensemble. However, this ensemble is hard proof that you totally can stay cozy and remain stylish at the same time in the colder months.