While working as a nurse in London, Squires sought singing jobs; she met agent Joe Kay, who got her night time work in various clubs. Squires performed at an East End club that gave her the name Dorothy, which she liked and adopted as her stage name. Squires did most of her work with the orchestra of Billy Reid, who was her partner for many years. After she joined his orchestra in 1936, he began to write songs for her to perform.