Want to inject your closet with some fashion-forward dapperness? Wear a red plaid long sleeve shirt with brown chinos. Burgundy leather casual boots will inject a hint of class into an otherwise standard ensemble. In the colder months, when comfort is essential, it can be easy to surrender to a less-than-stylish look in the name of functionality. However, this look proves that you can actually stay warm and remain equally stylish during the colder months. This ensemble demonstrates that figuring out how to dress well over 30 is totally doable.