Mrs.Donnelley was one of James's first clients and became aware of his talents through her friend, James's mother, Louise Brega James. Many of James's first clients were friends of his mother and his family who lived in Chicago dating back to the 1860s.
Less than five hats are known to exist from early in James's career. Although widely attributed to James, there is mystery surrounding its history: a handwritten label featuring the name "Mme. de Launay". In the first few years of his business, James was know to have worked with a milliner and friend of the same name, but if James owned the business from 1928 on why is her name hand written on the label inside? As with many of the fine details of James's history, elements of this time in his life remain uncertain.