Born in Bari, Boccasile was the son of a perfumer. Early in his youth he lost his left eye when a drop of quicklime fell in it while he drank from a fountain. Nonetheless, he showed a precocious aptitude for design and completed studies at the fine art school of his home town.
After the death of his father in 1925, he moved to Milan in order not to be a burden on his family. Despite some initial difficulties, he eventually gained a post at the Mauzan-Morzenti Agency. Over the next few years he produced posters and illustrated fashion magazines and gained fame for his sensual renderings of the female form.
Following the lead of fellow poster artist Achille Mauzan, Boccasile went to Buenos Aires for a time where he met his future spouse Alma Corsi. Alma Corsi. He then leaves again for Paris, where he had an issue of the “Paris Tabou” excellent review dedicated to his work and participated in the 1932 Salon des Independants. Returning to Milan, he opened a publicity agency called ACTA in Galleria del Corso with his friend Franco Aloi, and it is here that he found his real creative outlet. He illustrated for the Italian periodicals "La Donna" (1932), "Dea" and "La Lettura" (1934), "Bertoldo" (1936), "Il Milione" (1938), "L'Illustrazione del Medico" (1939), "Ecco", "Settebello" and "Il Dramma" (1939) and designed many book covers for the publishers Mondadori and Rizzoli'.
A supporter of Benito Mussolini, Boccasile produced propaganda material for the government. This included several racist and anti-semitic posters. After the war he was imprisoned and tried for collaborating with the Fascists and although acquitted, he remained an outcast. He could not find work for a few years as his signature was feared by prospective employers.
Nonetheless, he supported himself by doing erotic sketches for English and French publishers, and by 1946, after slightly changing his style, Boccasile was back at work. He set up his own agency in Milan where he created memorable posters for Paglieri cosmetics, Chlorodont toothpaste, and Zenith footwear, all bearing his signature.
He died prematurely in Milan, from bronchitis and pleurisy, in 1952.