Chester Barrie was founded in London in 1935 by Simon Ackerman. Based in the US, Ackerman visited London regularly, and inspired to create an English look for the American market, set up UK manufacturing locations with his sons Raymond and Myron. In the process they built a brand that is highly regarded the world over. Indeed, Ackerman was a pioneer on Savile Row, creating ready-to-wear tailoring with the look and feel of the best of bespoke The name itself came from Ackerman's desire to have an English sounding moniker; Chester was derived from the Roman city of the same name, near where he had established his factory, while Barrie came from JM Barrie, the author of Peter Pan, whose name, Ackerman thought, sounded particularly English.

Chester Barrie opened its first store on Savile Row in 1937 and the business has maintained a presence there ever since. The brand has Over 80 years of Savile Row tailoring history and customers have included Sir Winston Churchill, Cary Grant and Frank Sinatra, who were attracted by the brand's classic tailoring, beautiful fabrics and fine attention to detail. This continuing tradition and attention to detail and fine craftsmanship has seen the brand grow and today's clientele come from the varied worlds of business, finance, academia, and the arts.