Today the whole dressing code is fucked up in both the private and public sectors, even in the mob (except for the yakuza maybe). People are wearing "rainbow" shirts under suits and also some type of funny sneakers and pink socks, or they come dressed on meetings or at work like they live in some jungle or walked in their local bar or something.

Back in the old days, most of the old racketeers came from very poor background and when they made their riches, they wanted to express it by wearing expensive tailor-made suits, with the golden clips and diamond belts, including pinky rings and white or green fedoras. It was their mentality at the time because of their poor history, same as when some of the old black drug dealers and later old hip hop artists became rich and famous and also began wearing thick gold chains, diamond rings, gold teeth and fur coats. If you want to test poor man's character, give him money and power and you'll witness a different picture, although to be honest the old racketeers and atists were the "lesser evil" but still they created the base of all future OC in the US, especially in Chicago.