Wear some black and white gangster shoes and see what happens. If you want to dress like an old school Gangster, you're going to need to dress like the part with a flashy gangster style suit and finish the look with some black and white gangster shoes. These flashy black and white cap toe dress shoes feature that 1940s gangster style in a big way. You can wear these black and white dress shoes with a number of black and white stripe suits that you'll find at Contempo Suits. Medium Width.