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 several from Eastern Europe and Central Asia. This particular cap may have come from that area, or have Ottoman origins.

Many society families kept costumes for use in private theatricals or charades and notes on some of the non-theatrical Messel costumes indicate that he too had a 'dressing up' box. It is possible that he also wore them at fancy dress balls, which were a popular recreation among high society in the early and mid 20th century.

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.