A black overcoat and black plaid dress pants are absolute staples if you're picking out a dapper closet that holds to the highest sartorial standards. For times when this look appears too perfect, play it down by finishing with a pair of black suede chelsea boots. This one is an appealing idea when it comes to a knockout look that will take you from summer to fall. This combination proves that staying fashionable as you move into your 40s is totally doable.