For something more on the cool and laid-back side, opt for this combo of a grey cardigan and black jeans. To bring a little flair to this look, add a pair of black leather double monks to this ensemble. In the colder months, when practicality is a must, it can be easy to surrender to a less-than-stylish outfit in the name of functionality. However, this outfit is a stark illustration that you can actually stay cozy and remain stylish at the same time during the colder months.