After his return to London, Mr Ackerman became a leading figure in the British fashion circles before WWII. He was a far sighted man and saw his opportunity to establish his name and product in England's tailoring heartland, Savile Row.
He opened his first store on London's Savile Row in 1937. His one concern was that of his name, (or more accurately the name of his store) which he felt at the time was not "English" enough and he was keen to appeal to a local customer as well as an American one.
It is not exactly known how he decided upon Chester Barrie but it is understood that he wanted to have an English-sounding name. So he decided upon Chester (the English city in the north of England) and "Barrie" (as in J.M. Barrie, author and play write of Peter Pan fame).
London in the 1930's was the international centre of male elegance, with its famous streets Savile Row (for suits) and Jermyn Street (for shirts), and Chester Barrie thrived in this heady environment. Simon Ackerman's customers included the likes of Winston Churchill and later such luminaries as Frank Sinatra and Cary Grant. Savile Row and Jermyn Street.
During World War II Chester Barrie was involved in the war effort, providing hand-made uniforms for officers of the American forces.