Early in her career, when she was twenty-seven, Lempicka could hardly help being flattered by the attention given her work by the swashbuckling Italian poet and political leader, Gabriele D'Annunzio. The two got in touch with each other immediately, but their's would not be a lasting relationship. In 1925, the year D'Annunzio visited Lempicka's Milan exhibition, the "Commandatore" was sixty-two, which may well explain Lempicka's resistance to the advances of the spendthrift erotomaniac, despite all the persuasive means at his disposal to seduce her. The two players each took up their stage role, participating in tireless and vaudevillian comings and goings lasting for several days. The prevarications of the << Polish woman>> were noted by the palace housekeeper (herself subjected to the poet lecherous advances, whose ardor she sought to quell) in a quite cruel series of diary entries. These writings were rediscovered around 1975, and, to the great displeasure of Lempicka, were published straight away by Franco Maria Ricci, in a luxury edition! In 1984, the same diary served as source material for a stage play entitled Tamara.

Count Emanuele de Castelbarco (1884-1964), poet, editor, and patron of the arts, directed the Bottega di Poesia in Milan, an avant-gardist gallery where Lempicka was granted her first show. The count was also a painter, as is confirmed in an article by Jacqueline d'Hariel, which appeared in the December 1933 issue of Une Semaine de Paris, and which chronicles a reception given by Lempicka in her rue Méchain studio: "The occasion was in celebration of Castelbarco's first show at the Quatre Chemins. Castelbarco is Toscanini's son-in-law, and it was he who, in 1928 (actually 1925), had organized a first exhibition for Tamara de Lempicka in his Milan gallery. This party was an extremely gay affair, with several fans playing the accordion and the guitar, etc." There followed a long list of all the rich and famous of Paris who attended this reception.
The same year, Castelbarco went on to exhibit at the Salon des Surindépendents. In 1936, he participated in the Venice Biennale and, over the next years, had several shows in New York and Los Angeles.

By now, Lempicka had assimilated Lhote's revised brand of cubism; his teachings had left her with a taste for simplified volumes. And, from the Quattrocento masters, she retained, instinctively, the "linea serpentina". Her work of this period conveys the pleasure of using tonal gradations to model the spheres and cylinders with which she built up the bodies of her figures. Partial to a certain monumentalism, Lempicka chose her female models accordingly: whether naked or dressed, they are solidly and powerfully built, yet indisputably female. A certain pictorial aggressivity in her works of this period links them to the Neue Sachlichkeit painters across the Rhine. Frequent stays in Italy, together with the discovery of "Realismo Magico" gradually moderated this approach.