This portrait is one of only four important commissions for the artist during 1912, the other three being of Mrs. G. Blumenthal (Brooklyn Museum), Madame Josephina Alvear de Errazuriz (loc. cit. under lot 7) (Location unknown) and the Marchesa Dora di Rudini (Location unknown). The latter portrait of the Marchesa was the probable cause of the limited number, her erratic timekeeping eventually causing him to abandon the prolonged project in the middle of November. While Boldini had initially conceived the portrait of Madame de Gillespie as a full-length composition, the final format was employed in other works after 1900, notably his self-portrait of the previous year (Museo Boldini, Ferrara). The portrayal of the sitter glancing to one side, also recalls the celebrated portrait of Cléo de Mérode (Private Collection). This, combined with her beauty and the striking cyclamen hue of her loose dress provide the same impact as many of the more elaborate compositions within the collection.

While little is known of Madame de Gillespie, she probably received her introduction to the artist through Henri Letellier, whose wife was portrayed in the renowned work of 1907. Wildenstein's unusual title of "La Dame de Biarritz" may have been the suggestion of Baron Maurice de Rothschild, as there is no other literary reference to this sobriquet.