A black leather bomber jacket and charcoal skinny jeans are indispensable menswear must-haves if you're figuring out an off-duty closet that holds to the highest sartorial standards. If you need to easily ramp up this look with one single piece, complement this getup with a pair of charcoal leather casual boots. This combo demonstrates that as a 40-something guy, you have a wide range of sartorial options.