For something on the casually cool side, you can rock a grey cowl-neck sweater and blue ripped jeans. When it comes to footwear, go for something on the smarter end of the spectrum and finish your look with black cutout leather ankle boots. During the colder months, when practicality is a must, it can be easy to surrender to a less-than-stylish getup in the name of convenience. This getup, however, is a vivid example that you totally can stay cozy and remain incredibly chic during the colder months.