Vintage 1960s Fedora by James Lock & Co. for Brooks Brothers
While we're still on the subject of endangered sartorial species, various indigenous strains of the American Male's head wear have been reported to be on the verge of extinction for going on 50 years now. Some historians have traced the origins of the hat's demise to that cold and wintry day in January of 1961 when President-elect John F. Kennedy chose to brave the elements sans top hat, derby, or fedora for his swearing-in ceremony.
Yes, hard as it is to believe, but once upon a time the broad-brimmed hat, and not the baseball cap, was the head wear of choice for the discerning American man. No, really, I've done some minor sleuthing and it appears to be true. Furthermore, how one wore the hat provided some insight into the character and attitude of the wearer. This idea was touched upon in a recent episode of the HBO drama Boardwalk Empire when the writers emphasized Al Capone's evolution from a merry prankster and generally irresponsible ne'er-do-well within the Torrio organization to a more serious-minded, focused vice-lord by highlighting Scarface Al's switch from the 8-piece pie cap, or newsboy, to the more staid and refined fedora (another example that comes to mind is the scene in The Big Sleep when Humphrey Bogart's Philip Marlowe goes undercover into Geiger's "bookstore" front as a collector of rare book editions, primarily by taking his tie off, leaving his collar buttoned, and turning the brim of his hat up all the way around).
Nevertheless, Capone must have retained some of the more flamboyant aspects of his personality when he took control of Torrio's South Side gang (immortalized in the annals of crime as the Chicago "Outfit"), as evidenced by this photo taken of Chicago furniture salesman "Al Brown":
As you can see, the brim is upturned on only one side while the hat is tilted rakishly toward Capone's left eye. The whole thing exudes a devil-may-care, almost swashbuckling effect that is further hinted at by the trace of a smirk darting across Capone's face. But it all comes back to the flippant swagger in the snap of the brim and the tilt of the hat - it suggests the brash humor of a man who once was quoted as saying that you can get farther with a kind word and a gun than you can with just a kind word.
Having only seen the fedora worn like this in mugshots and police line-ups from Prohibition-era Chicago, I assumed that this must have been the preferred style of the Chicago Outfit for their pearl grey fedoras. Recently, however, I came across a few photos of that suave and debonair leading man from the Golden Age of Hollywood, William Powell, known for his dapper turns in such films as The Thin Man and Manhattan Melodrama. (never has a house servant appeared so magnificent in white tie and tails than Powell in My Man Godfrey).
Since there doesn't appear to be any record of Powell having portrayed a gangster during the early 1930s(although he did appear in The Great Gatsby in 1926 and The Hoodlum Saint 20 years later), it seems unlikely that these are publicity stills for a film. More likely, the hat with the brim snapped up to one side was a style worn by all self-styled dandies of the Roaring Twenties, be he racketeer, matinee idol, or some other form of box-office attraction.