None of these fellas today....NONE of them, could ever hold a candle to the way wiseguys dressed from yesteryear. Especially guys from New York City! It's not even a contest.
Everybody, not just Mob bosses, dressed better in thr Fifties and earlier. Unless you were a manual worker, you wore a suit, hat and tie to work. Mob guys dressed to the hilt to "fit in" with "legitimate" people and to show "class," which meant something in those days. And, the only men who wore track suits were track runners.