Reach for a black shearling jacket and light blue ripped skinny jeans, if you prefer to dress for comfort without looking like you don't care to look dapper. A pair of beige suede chelsea boots easily levels up the outfit. During the colder months, when comfort is key, it can be easy to settle for a less-than-stylish getup. This getup, however, is a shining example that you can actually stay snug and remain stylish at the same time in the colder months. And if we're talking casual clothing for over-30 gentlemen, this outfit is perfect.