At The Art of Manliness (a website that celebrates guys in an online barbershop sort of way), author Brett McKay occasionally highlights Rat Pack Sinatra (the cool as steel, urban man's man), giving advice on how to emulate his style.
"Cock your hat - angles are attitudes." - Sinatra
One article, "Bringing Back The Hat", showcases different types of hats and how to wear them. Near the end is a section on the various ways that Sinatra would wear his fedora.
There's another entry on Sinatra Slang.
It's interesting to discover what the modern public thinks about classic films stars.