At his graduation from gymnasium in 1889, Ivan submitted myriad documents to the admissions committee at the Imperial Academy of Arts in Saint Petersburg. To his delight, he was accepted and, shortly afterward, moved to the exciting and artistically inspirational capital of Romanov Russia. A number of Academy professors, among them Ilia Repin and the landscape painter Arkhip Kuindzhi, had been early proponents of the Wanderers movement, and many of their pupils drank deeply at this well of Russian realist art. Ivan was an enthusiastic disciple, but, in 1891, after having completed his initial courses, he was called up for military service and enlisted in the Imperial Cavalry. Ivan was able to leave the army in 1894 with the rank of lieutenant, and remained a member of the Officers’ Reserve Corps.

From the mid-1890s until his graduation in late 1901, Djeneeff reveled in the lifestyle offered by membership in the Academy. Toward the end of the decade he participated actively in group exhibitions with other Academy students, and during the summer of 1898 was chosen to accompany the Veselovskii archaeological expedition to Samarkand as a staff artist. Deeply affected by the sights and sounds of Central Asia, Djeneeff developed a lifelong fascination with “Oriental” culture - albeit a Western and romanticized version of what he had seen in there.