Pictures in the 1940s and 1950s shows these guys mostly insuits often with fedora type hats
Even earlier
And yes,they probably wanted to fit it with the businessmen and politicians and other upper crust people rather that rely on committing street crimes
Back then if they were together at a crap game or social club,they probably dressed more casually but not in ripped jeans an a T-Shirt or a baseball cap turned backward
Somehow they managed to dress well and still not get exposed as being part of a criminal society for many years
I think rich people including politicians these days often are associating with people dressed like bums as long as they have some kind of reputation or fame or wealth and can influence large followings.
I think that one of the biggest components figuring into the way so-called 'wiseguys' dress today has mostly to do with the era they find themselves in. They're dressing habits only mirror the larger population and the mindset in America today.
The average businessman, unless he is on Wall Street or operates from Park Avenue as a lawyer or top corporate official, generally does not dress in a business suit or even in dress slacks and a button down shirt. Say what you like about that, but it's just not the way it is anymore.
The average man or woman dresses much more casual today -- even when they go out to dinner in a nice restaurant. How many people in the finest of restaurants even wear a sports jacket nowadays? Not many! 90% of the finest restaurants in NYC don't even require a 'jacket' anymore.
....sign of the times.
I dress in a suit or sport coat when Im going out to dinner. Id feel
Funny not doing so.
I enjoy dressing up also...but the occasion has to call for it. Of course, at a wedding or other formal event I'm gonna wear a suit and tie. If I'm going to Manhattan for dinner at a top place like Delmonico's or the Bull & Bear Restaurant in the Waldorf Astoria Hotel, then I would also dress my best. Or, if I think it's appropriate, I'd at least wear a sports jacket and an open collared dress shirt. Dinner out with certain friends or couples, etc.
But today, many of the finest dining establishments on Manhattan's Upper East Side don't even require a sports jacket (although I personally would feel underdressed not to wear one.) Dress slacks and shirt, dress shoes, etc. Thats how many people go today. I think they refer to it as 'smart casual.'
And I'm talking about top joints that are multimillion-dollar venues. Drop dead gorgeous Big Apple eateries that draw a celebrity and upper crust fine dining crowd, where the average tab can run $200-$400 or more per head for supper. These are not your average run-of-the-mill restaurants...The world changed.
In the outer boroughs like Brooklyn, Queens, Bronx, Long Island, etc., at top places, its even more relaxed.
You'll still see most people dress very nicely. They don't dress like slobs. But sports jackets and suits are generally a rarity, unless its a business meeting or some other type event.
Do I personally agree with it. Not necessarily. Like I mentioned, I enjoy dressing up. But this is today's vibe. Nowadays, to wear a suit or sports jacket to most places you'd stick out like a sore thumb and almost look inappropriate and stuffy.
PS: But no doubt, in years to come, they'll be a reverse trend. What do they say? "Everything old becomes new again."
Most everything in life is cyclical.
