A black shearling jacket and dark brown chinos matched together are the ideal look for those dressers who prefer cool and casual combos. Go ahead and complement this outfit with chelsea boots for an added touch of style. You might think that just because it is snowing outside you have to sacrifice on style, but it's just not true, and this outfit is a striking example. This ensemble is the perfect answer to the question of how to dress your age as you move into your 40s.