Like many designers, Messel was fascinated by costume and crafts. He collected items not particularly because he was researching for a specific production, but simply because they took his fancy. He amassed a collection of hats and headdresses, including ethnic examples from Europe, Eastern Europe and Central Asia and others from various periods. This particular example is in the style of an 18th century tricorne (i.e. having three points).

Inside the hat is the label of B J Simmons, a famous theatrical costumier. It is possible that the hat was used in a Messel production, but Simmons also hired out costumes for costume and fancy dress balls. Fancy dress balls were a popular recreation among high society in the early and mid 20th century. Alternatively, many society families kept costumes for use in private theatricals or charades and it is possible that Messel hired the hat for a ball and it then found its way into his 'dressing up' box.

Oliver Messel (1904-1978) was Britain's leading theatre designer from the early 1930s to the mid 1950s, working in every aspect of entertainment - ballet, drama, film, musical, opera and revue - as well as in interior decoration and textile design. His lavish, painterly and romantic designs informed by period styles, were perfectly in tune with his times and earned him an international reputation. By 1960, however, Messel's style had become unfashionable, having no sympathy with the new 'kitchen sink' school of theatre. He increasingly concentrated on his non-theatrical painting and designing and eventually retired to the Caribbean, where he began a new career designing and building highly idiosyncratic luxury villas.