Consider pairing a black shearling jacket with dress pants - this look will surely make a statement. We love how this whole ensemble comes together thanks to dark brown chelsea boots. During the colder months, when warmth is imperative, it can be easy to surrender to a less-than-stylish outfit. This outfit, however, is a shining example that you totally can stay toasty and remain stylish at the same time in the colder months. This is a practical illustration of how to dress with style and look age-appropriate.