Aquascutum, the clothing company owned by Jewish businessman Harold Tillman, has gone into administration putting 250 jobs at risk.
Fashion businessman Mr Tillman, the former chairman of Jaeger, bought the luxury British brand, which dressed Winston Churchill and the Queen Mother, from its Japanese owners in 2009.
Mr Tillman became chairman of the British Fashion Council in 2008 and is a member of Highgate Synagogue.
The administration came after Mr Tillman sold his stake in Jaeger, whose operations were tied in with those of Aquascutum.
Aquascutum was founded in 1851 by tailor John Emary. It was named after the Latin for water shield after it developed the first waterproof wool. In its early days it was best known for a style of trenchcoat worn during the First World War. The business's clothes have been worn by Lady Thatcher, Humphrey Bogart and Cary Grant.
Mr Tillman and Ms Earl bought Aquascutum despite it making losses of around £24 million. Over the last three years, shareholders have invested around £30 million in the company.