What crime family over the years really hasnt ever had the reputation of having guys that looked all that great? Dressed like shit with absolutely not giving two fucks about what they wore or how good their hair & teeth looked.

On the other hand you have families like the Gambinos who seemed to have a strict dress code on the street and took pride in their hygiene and appearance. Especially during Gottis reign.

Hard to say as each family had their fair share of guys who liked to dress up and look the part.

Alright fair enough let's get a little bit more specific....

What crime family has had the most good looking bosses and which one would you say to put it nicely have been lacking in the attractive department?

The Chicago Outfit had some pretty gnarly-looking characters.

Agreed. Lombardo looked like a monkey especially when he was older.

Anthony (Tony Roach) Rampino from the Gambinos and Roy DeMeos cousin Joey Gugliomo and Anthony saw tees uncle Robert Senter or Sentner as he spelled it were some Grave Looking individuals

No Diddy, but Handsome Johnny Rosselli was a looker, but he's the exception, not the rule lol.

Aint "she" a "beauty" Lol lol......

Lots of mob guys are getting their teeth done- porcelain veneers or caps. Also hair transplants.

Looking at the photos in "Donnie Brasco" and "King of the Godfathers," I'd have to say Bonannos were the ugliest.

LOL all big families had those guys, often also the most scary guys haha.

I would've had Mad Sam whacked for taking that photo with that pose alone, making the Outfit look bad.

Thats right but dont forget money comes first in the Mafia, followed by psychological problems in second place.

No Diddy, but Philly probably has the best looking wiseguys. But looks seem to be a priority for them they stay in shape.