I think the gangsters from the 1920s through the 40s dressed the best as far as the American Mafia is concerned. Maybe even 1960s, but after that it kinda went downhill. There were still some dapper gents, don't get me wrong, but the era I mentioned beats them all.
IMO, whether it was 1920, 1930, 1940, 1950, 1960, 1970, 1980....on up...The old-timers....the REAL wiseguys, who cut their teeth and made the mob - "THE MOB" - were the ones who set the standard of dress. And you didn't have to be a boss or have a million dollars to dress like like a boss or look like a million dollars. Lol
The fact of the matter is, whether you were a so-called associate, soldier, captain, underboss, consigliere or Family boss. If you had some class and knew what was what, were successful in "The Life," had some money and some taste, you dressed the part and wore the best....and looked like exactly what you were...a fucking wiseguy!....and you dressed to the nines!
THAT was the goal for 99.9999% of street guys who grew up in poverty and strived for something better in life....and went into "the life." Because it was also considered a sign of "success."
