Winston Churchill

In 1940, Winston Churchill posed for a picture that made him look more like a Chicago hoodlum than the British Prime Minister.

He held a Thompson submachine gun, popular with US gangsters during Prohibition. There was also his signature cigar, the bowler hat, the spotted bow tie, and the immaculate chalk-stripe flannel suit. 

The suit was made by the Savile Row tailors, Henry Poole, with woven cloth supplied by Fox Brothers of Wellington, Somerset.

BBC News has just published an interesting article about Churchill’s battle with depression to which he referred to as his "Black Dog".

Mentally challenged yet sartorially triumphant.

Winston Churchill | Dispatch