This combination of a brown herringbone overcoat and dress pants couldn't possibly come across as anything other than outrageously sharp and polished. Complete your ensemble with tassel loafers and you're all set looking spectacular. During the colder months, when functionality is prized, it can be easy to surrender to a less-than-stylish ensemble in the name of practicality. However, this ensemble proves that you can actually stay comfy and remain stylish at the same time in the colder months. Wondering what to wear as you step into your 50s? This getup is the perfect answer.