After completing his studies, he became a portrait painter and commissions for theatre work soon followed, beginning with his designing the masks for a London production of Serge Diaghilev's ballet Zephyr et Flore (1925).

Subsequently, he created masks, costumes, and sets – many of which have been preserved by the Theatre Museum, London – for various works staged by C. B. Cochran's revues through the late 1920s and early 1930s.

[4] For film his costume designs include The Private Life of Don Juan (1934); Scarlet Pimpernel (1934); Romeo and Juliet (1936); The Thief of Bagdad (1940); and Caesar and Cleopatra (1945).

He was Art Director on Caesar and Cleopatra (1945), On Such a Night (1956) and Production Designer on Suddenly Last Summer (1959), for which he was nominated for the Academy Award.

The lavishly ornate Oliver Messel Suite, which the hotel advertises as Elizabeth Taylor's favourite place to stay in London, combines baroque and rococo styles with modernist sensibility and a considerable dose of fantasy.

The warmth, colour and vibrancy of the tropics seemed to liberate new sources of energy and imagination, leading him to what eventually became a whole new career in designing, building and transforming homes.

With the help of his companion Vagn Riis-Hansen, with whom he had a 30-year relationship,[14] and a Barbadian staff, Messel transformed it using the trademarks of his theatrical design: slender Greek columns, flattened arches, white-on-white interiors splashed with bright spots of colour, elaborate plaster mouldings – an easy mix of baroque and classical.

He designed and built Mango Bay from scratch and was commissioned by the Barbados government to restore the old British officers Garrison headquarters in Queens Park, creating an elegant adaptation of it to a theatre and art gallery.