Uber stylish, this casual pairing of a tan shearling jacket and brown chinos will provide you with wonderful styling possibilities. Get a bit experimental with shoes and tone down this outfit by rocking dark brown leather work boots. In the winter season, when practicality is paramount, it can be easy to surrender to a less-than-stylish look in the name of functionality. However, this look is hard proof that you can actually stay comfy and remain stylish in the winter season. Wondering how to nail casual dressing as you navigate your 20s? This combination is the perfect answer.