09/19/2013 09:00 am ET Updated Dec 06, 2017

Frank Sinatra's Style Almost Distracts Us From His Bad-Boy Image (PHOTOS)

What is it about bad boys that makes them look so good? We here at HuffPost Style have serious crushes on Al Pacino, James Dean and every rabble-rouser in between, so we decided to do some stylish digging to find the baddest bad boy of them all.

Well, look no further than Frank Sinatra, the original Rat Pack-er who was never once underdressed -- a pretty suave way to avoid scrutiny, in our opinion. Sinatra looked so good, you (almost) didn't notice his ties to the mafia and organized crime. In fact, Sinatra was so smooth, he and his cronies Dean Martin and Bing Crosby sang about style in 1964's "Robin and the 7 Hoods" (see above).

"You either got or you haven't got style," Sinatra crooned. Thank goodness he riffed further on the idea in interviews with Bill Zehme for his biography, "The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Living." Below, the sartorial wisdom Ol' Blue Eyes shared:

Tilt your fedora for extra attitude.

frank sinatra



Cufflinks are essential -- but no other jewelry is necessary.


And let your shirtsleeves extend well past your jacket.

shirt sleeve

The wider the lapel, the better.


Vests elevate suits to the next level


And so do patterns, for that matter.

checked jacket

pattern suit

Pants must always be pressed perfectly.

pressed pants

Black is the only acceptable shoe color.


Make sure to fold a pocket square perfectly.

pocket square

pocket square

The fit of the suit is of the utmost importance.


Today's tastemakers don't come close:

Stylish Male Celebs

Want more? Be sure to check out HuffPost Style on Twitter, Facebook, Tumblr, Pinterest and Instagram at @HuffPostStyle.