For a look that looks as chill as it can get, consider wearing a tan hoodie and skinny jeans. A great pair of dark brown leather chelsea boots is an effortless way to power up this outfit. During the colder months, when practicality is crucial, it can be easy to surrender to a less-than-stylish look. But this look is a shining example that you totally can stay comfy and remain equally stylish in the colder months.