This pairing of a grey wool blazer and navy dress pants is a safe option when you need to look extra smart and elegant. When not sure about the footwear, stick to dark brown leather derby shoes. You might think that just because you need to get bundled up you have to sacrifice your style, but that's just not true, and this outfit is hard proof. Wondering how you should dress as you age into your 40s? This getup is the perfect answer.