Samson Wertheimer became a leading art dealer in London, and Asher continued the business from premises on Bond Street after his father's death.
Mr and Mrs Wertheimer commissioned Singer Sargent to paint two portraits to celebrate their 25th wedding anniversary in 1898, and ten more commissions followed in the next decade: Sargent's portrait of Asher Wertheimer was a success when exhibited at the Royal Academy of Arts, later described by Robbie Ross in The Art Journal in 1911 as "the only modern picture which challenges the Doria Velázquez at Rome".
Sargent was asked to paint a second version of Flora, in which she is seated and dressed in black, which was better received.
The first portrait of Flora Wertheimer in a white dress was inherited by her daughter Hylda and later came into the collection of the New Orleans Museum of Art.
A 1908 portrait of Betty is held by the Smithsonian American Art Museum, in Washington, DC.